Document:

EX-10.1

 Exhibit 10.1 
  

 
  

COMMON UNIT PURCHASE AGREEMENT 

by and among 
 TEEKAY
OFFSHORE PARTNERS L.P. 
 and 

THE PURCHASERS NAMED ON SCHEDULE A HERETO 
  

 
  

 TABLE OF CONTENTS 

 

							
	 ARTICLE I DEFINITIONS
	  	 	1	  
			
	 Section 1.1
	 	Definitions	  	 	1	  
		
	 ARTICLE II AGREEMENT TO SELL AND PURCHASE
	  	 	5	  
			
	 Section 2.1
	 	Sale and Purchase	  	 	5	  
	 Section 2.2
	 	Closing	  	 	5	  
	 Section 2.3
	 	Mutual Conditions	  	 	6	  
	 Section 2.4
	 	Each Purchaser’s Conditions	  	 	6	  
	 Section 2.5
	 	The Partnership’s Conditions	  	 	7	  
	 Section 2.6
	 	Partnership Deliveries	  	 	8	  
	 Section 2.7
	 	Purchaser Deliveries	  	 	9	  
	 Section 2.8
	 	Independent Nature of Purchasers’ Obligations and Rights	  	 	9	  
		
	 ARTICLE III REPRESENTATIONS AND WARRANTIES OF THE PARTNERSHIP
	  	 	10	  
			
	 Section 3.1
	 	Existence	  	 	10	  
	 Section 3.2
	 	Purchased Units; Capitalization	  	 	10	  
	 Section 3.3
	 	Subsidiaries	  	 	11	  
	 Section 3.4
	 	No Conflict	  	 	13	  
	 Section 3.5
	 	No Default	  	 	13	  
	 Section 3.6
	 	Authority	  	 	13	  
	 Section 3.7
	 	Approvals	  	 	13	  
	 Section 3.8
	 	Compliance with Laws	  	 	14	  
	 Section 3.9
	 	Due Authorization	  	 	14	  
	 Section 3.10
	 	Valid Issuance; No Options or Preemptive Rights; Title	  	 	14	  
	 Section 3.11
	 	No Registration Rights	  	 	14	  
	 Section 3.12
	 	Periodic Reports	  	 	15	  
	 Section 3.13
	 	Litigation	  	 	15	  
	 Section 3.14
	 	Insurance	  	 	15	  
	 Section 3.15
	 	Internal Accounting Controls	  	 	15	  
	 Section 3.16
	 	No Material Adverse Change	  	 	16	  
	 Section 3.17
	 	Certain Fees	  	 	16	  
	 Section 3.18
	 	No Side Agreements	  	 	16	  
	 Section 3.19
	 	No Registration	  	 	16	  
	 Section 3.20
	 	Investment Company Status	  	 	16	  
	 Section 3.21
	 	Form F-3 Eligibility	  	 	16	  
	 Section 3.22
	 	Passive Foreign Investment Company	  	 	16	  
	 Section 3.23
	 	Tax Status	  	 	16	  
	 Section 3.24
	 	Foreign Corrupt Practices Act	  	 	17	  
		
	 ARTICLE IV REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS
	  	 	17	  
			
	 Section 4.1
	 	Existence	  	 	17	  
	 Section 4.2
	 	Authorization, Enforceability	  	 	17	  

  
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	 Section 4.3
	 	No Breach	  	 	18	  
	 Section 4.4
	 	Certain Fees	  	 	18	  
	 Section 4.5
	 	No Side Agreements	  	 	18	  
	 Section 4.6
	 	Investment	  	 	18	  
	 Section 4.7
	 	Nature of Purchaser	  	 	19	  
	 Section 4.8
	 	Restricted Securities	  	 	19	  
	 Section 4.9
	 	Legend	  	 	19	  
	 Section 4.10
	 	Short Selling	  	 	19	  
	 Section 4.11
	 	Trading Activities	  	 	20	  
	 Section 4.12
	 	Short Selling Acknowledgement and Agreement	  	 	20	  
	 Section 4.13
	 	Purchaser Investigation; Partnership Projections	  	 	20	  
		
	 ARTICLE V COVENANTS
	  	 	20	  
			
	 Section 5.1
	 	Taking of Necessary Action	  	 	20	  
	 Section 5.2
	 	Other Actions	  	 	20	  
	 Section 5.3
	 	Payment and Expenses	  	 	20	  
	 Section 5.4
	 	Use of Proceeds	  	 	21	  
	 Section 5.5
	 	Delivery of Purchased Units	  	 	21	  
		
	 ARTICLE VI INDEMNIFICATION
	  	 	21	  
			
	 Section 6.1
	 	Indemnification by the Partnership	  	 	21	  
	 Section 6.2
	 	Indemnification by Purchasers	  	 	21	  
	 Section 6.3
	 	Indemnification Procedure	  	 	22	  
		
	 ARTICLE VII MISCELLANEOUS
	  	 	23	  
			
	 Section 7.1
	 	Interpretation and Survival of Provisions	  	 	23	  
	 Section 7.2
	 	Survival of Provisions	  	 	23	  
	 Section 7.3
	 	No Waiver; Modifications in Writing	  	 	23	  
	 Section 7.4
	 	Binding Effect; Assignment	  	 	24	  
	 Section 7.5
	 	Communications	  	 	24	  
	 Section 7.6
	 	Removal of Legend	  	 	25	  
	 Section 7.7
	 	Entire Agreement	  	 	25	  
	 Section 7.8
	 	Governing Law	  	 	26	  
	 Section 7.9
	 	Execution in Counterparts	  	 	26	  
	 Section 7.10
	 	Termination	  	 	26	  
	 Section 7.11
	 	Recapitalization, Exchanges, Etc. Affecting the Common Units	  	 	26	  
	 Section 7.12
	 	Disclosure	  	 	26	  
			
	 Schedule A
	 	List of Purchasers and Commitment Amounts	  			
	 Schedule B
	 	Notice and Contact Information	  			
	 Schedule 3.13
	 	Litigation	  			

  

			
	 Exhibit A —
	  	 Form of Registration Rights Agreement

	 Exhibit B —
	  	 Form of Opinion of Perkins Coie LLP

	 Exhibit C —
	  	 Form of Opinion of Watson Farley & Williams LLP

  
 ii 

 Exhibit 10.1 

COMMON UNIT PURCHASE AGREEMENT 

This COMMON UNIT PURCHASE AGREEMENT, dated as of June 16, 2016 (as further defined below, this
“Agreement”), is by and among TEEKAY OFFSHORE PARTNERS L.P., a Marshall Islands limited partnership (the “Partnership”), and the purchasers listed on Schedule A hereof (each a “Purchaser” and
collectively, the “Purchasers”). 
 WHEREAS, the Partnership desires to sell to the Purchasers, and the
Purchasers desire to purchase from the Partnership, certain Common Units (as defined below), in accordance with the provisions of this Agreement. 

WHEREAS, in connection with the issuance of the Common Units pursuant to this Agreement, the Partnership and the Purchasers
will enter into a registration rights agreement (the “Registration Rights Agreement”), substantially in the form attached hereto as Exhibit A, pursuant to which the Partnership will provide the Purchasers with certain
registration rights with respect to the Common Units acquired pursuant hereto. 
 WHEREAS, in connection with the
Partnership’s recapitalization plan, at or prior to the Closing, the Partnership intends to (i) enter into a Preferred Unit and Warrant Purchase Agreement (the “Series D Purchase Agreement”) pursuant to which it will sell,
in a private placement (the “Series D Offering”) up to $200 million of Series D Cumulative Convertible Perpetual Preferred Units (the “Series D Preferred Units”) and related warrants (the “Series D
Warrants”), (ii) pursuant to the terms of a letter agreement between the Partnership and the holders of the Series C Preferred Units (as defined below) and related documentation setting forth the terms of the Series C transaction (the
“Series C Transaction”) to exchange a portion of the outstanding Series C Preferred Units for Common Units and exchange the remaining Series C Common Units, on a one-for-one basis, for a new series of preferred units of the
Partnership designated as 8.60% Series C-1 Cumulative Convertible Perpetual Preferred Units (the “Series C-1 Preferred Units”). 

NOW THEREFORE, in consideration of the mutual covenants and agreements set forth herein and for good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged, the Partnership and each of the Purchasers, severally and not jointly, hereby agree as follows: 

ARTICLE I 
 DEFINITIONS

 Section 1.1 Definitions. As used in this Agreement, and unless the context requires a different meaning,
the following terms have the meanings indicated: 
 “Affiliate” means, with respect to any Person, any
other Person that directly or indirectly through one or more intermediaries controls, is controlled by or is under common control with, the Person in question. As used herein, the term “control” means the possession, direct or indirect, of
the power to direct or cause the direction of the management and policies of a Person, whether through ownership of voting securities, by contract or otherwise. 

 “Agreement” has the meaning set forth in the introductory
paragraph, as amended, supplemented, continued or modified. 
 “Business Day” means a day other than
(i) a Saturday or Sunday or (ii) any day on which banks located in New York, New York, U.S.A. are authorized or obligated to close. 

“Closing” has the meaning specified in Section 2.2. 

“Closing Date” has the meaning specified in Section 2.2. 

“Commission” means the United States Securities and Exchange Commission. 

“Common Unit Price” has the meaning specified in Section 2.1(a). 

“Common Units” means the Common Units representing limited partnership interests in the Partnership having
the rights and obligations specified in the Restated Partnership Agreement. 
 “Exchange Act” means the
Securities Exchange Act of 1934, as amended from time to time, and the rules and regulations of the Commission promulgated thereunder. 

“Existing Registration Rights Agreement” means the Registration Rights Agreement, dated July 1, 2015, by
and among the Partnership and each of the Persons set forth on Schedule A thereto. 
 “General Partner”
means Teekay Offshore GP L.L.C., a Marshall Islands limited liability company. 
 “Governmental Authority”
means, with respect to a particular Person, any country, state, county, city and political subdivision in which such Person or such Person’s Property is located or that exercises valid jurisdiction over any such Person or such Person’s
Property, and any court, agency, department, commission, board, bureau or instrumentality of any of them and any monetary authority that exercises valid jurisdiction over any such Person or such Person’s Property. Unless otherwise specified,
all references to Governmental Authority herein with respect to the Partnership mean a Governmental Authority having jurisdiction over the Partnership, its Subsidiaries or any of their respective Properties. 

“Indemnified Party” has the meaning specified in Section 6.3. 

“Indemnifying Party” has the meaning specified in Section 6.3. 

“Law” means any federal, state, local or foreign order, writ, injunction, judgment, settlement, award,
decree, statute, law, rule or regulation. 
 “Lien” means any mortgage, claim, encumbrance, pledge, lien
(statutory or otherwise), security agreement, conditional sale or trust receipt or a lease, consignment or bailment, preference or priority or other encumbrance upon or with respect to any property of any kind; provided, however, that any charter or
services contracts to which the Partnership’s vessels are subject shall not be deemed Liens. 

  
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 “Marshall Islands LLC Act” means the Marshall Islands Limited
Liability Company Act of 1996, as amended. 
 “Marshall Islands LP Act” means the Marshall Islands Limited
Partnership Act, as amended. 
 “Material Adverse Effect” has the meaning specified in
Section 3.1. 
 “NYSE” means The New York Stock Exchange, Inc. 

“OLP GP” means Teekay Offshore Operating GP L.L.C., a Marshall Islands limited liability company. 

“Operating Company” means Teekay Offshore Operating L.P., a Marshall Islands limited partnership. 

“Operative Documents” means, collectively, this Agreement and the Registration Rights Agreement, or any
amendments, supplements, continuations or modifications thereto. 
 “Partnership” has the meaning set forth
in the introductory paragraph. 
 “Partnership Agreement” means the Fourth Amended and Restated Agreement
of Limited Partnership of the Partnership dated July 1, 2015, as amended to date. 
 “Partnership
Entities” and each a “Partnership Entity” means the General Partner, the Partnership and each of the Partnership’s Subsidiaries, other than those Subsidiaries which, individually, or in the aggregate, would not
constitute a “significant subsidiary” as defined in Regulation S-X. 
 “Partnership Related
Parties” has the meaning specified in Section 6.2. 
 “Partnership SEC Documents” has
the meaning specified in Section 3.12. 
 “Person” means an individual or a corporation,
limited liability company, partnership, joint venture, trust, unincorporated organization, association, government agency or political subdivision thereof or other form of entity. 

“Preferred Units” has the meaning specified in Section 3.3(c). 

“Property” means any interest in any kind of property or asset, whether real, personal or mixed, or tangible
or intangible. 
 “Purchase Price” means, with respect to a particular Purchaser, the amount set forth
opposite such Purchaser’s name under the column titled “Purchase Price” set forth on Schedule A hereto. 

  
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 “Purchased Units” means, with respect to a particular Purchaser,
the number of Common Units set forth opposite such Purchaser’s name under the column titled “Common Units” set forth on Schedule A. 

“Purchaser” and “Purchasers” have the meanings set forth in the introductory paragraph. 

“Purchaser Related Parties” has the meaning specified in Section 6.1. 

“Registration Rights Agreement” has the meaning set forth in the recitals hereto. 

“Representatives” of any Person means the Affiliates, officers, directors, managers, employees, agents,
counsel, accountants, investment bankers and other representatives of such Person. 
 “Restated Partnership
Agreement” means the Fifth Amended and Restated Agreement of Limited Partnership of the Partnership to be adopted by the Partnership prior to the Closing to set forth, among other things, the terms of the Series C-1 Preferred Units and the
Series D Preferred Units. 
 “Securities Act” means the Securities Act of 1933, as amended from time to
time, and the rules and regulations of the Commission promulgated thereunder. 
 “Series A Preferred Units”
has the meaning specified in Section 3.3(c). 
 “Series B Preferred Units” has the meaning
specified in Section 3.3(c). 
 “Series C Preferred Units” has the meaning specified in
Section 3.3(c). 
 “Series C Transaction” has the meaning set forth in the recitals hereto.

 “Series C-1 Preferred Units” has the meaning set forth in the recitals hereto. 

“Series D Offering” has the meaning set forth in the recitals hereto. 

“Series D Preferred Units” has the meaning set forth in the recitals hereto. 

“Series D Purchase Agreement” has the meaning set forth in the recitals hereto. 

“Series D Registration Rights Agreement” means the registration rights agreement to be entered into among the
Partnership and the purchasers of the Series D Preferred Units in the Series D Offering. 
 “Series D
Warrants” has the meaning set forth in the recitals hereto. 
 “Short Sales” means, all
“short sales” as defined in Rule 200 promulgated under Regulation SHO under the Exchange Act, whether or not against the box, and forward sale contracts, options, puts, calls, short sales, “put equivalent positions” (as defined
in Rule 16a-1(h) under the Exchange Act) and similar arrangements, and sales and other transactions through non-U.S. broker dealers or foreign regulated brokers. 

  
 4 

 “Subsidiary” means, as to any Person, any corporation or other
entity of which: (i) such Person or a Subsidiary of such Person is a general partner or manager; (ii) at least a majority of the outstanding equity interest having by the terms thereof ordinary voting power to elect a majority of the board
of directors or similar governing body of such corporation or other entity (irrespective of whether or not at the time any equity interest of any other class or classes of such corporation or other entity shall have or might have voting power by
reason of the happening of any contingency) is at the time directly or indirectly owned or controlled by such Person or one or more of its Subsidiaries; or (iii) any corporation or other entity as to which such Person consolidates for
accounting purposes. 
 “Teekay” means Teekay Corporation, a Marshall Island corporation. 

“Teekay Offshore Holdings” shall have the meaning set forth in Section 3.4(a). 

“Walled Off Person” shall have the meaning set forth in Section 4.5. 

ARTICLE II 
 AGREEMENT
TO SELL AND PURCHASE 
 Section 2.1 Sale and Purchase. 

(a) Subject to the terms and conditions hereof, the Partnership hereby agrees to issue and sell to each Purchaser and each
Purchaser hereby agrees, severally and not jointly, to purchase from the Partnership, its respective Purchased Units, and each Purchaser agrees, severally and not jointly, to pay the Partnership the Common Unit Price for each Purchased Unit as set
forth in paragraph (b) below. The obligations of each Purchaser under this Agreement are independent of the obligations of each other Purchaser, and the failure or waiver of performance by any Purchaser does not excuse performance by any other
Purchaser or by the Partnership. 
 (b) The amount per Common Unit each Purchaser will pay to the Partnership to purchase the
Purchased Units (the “Common Unit Price”) hereunder shall be $4.55. 
 Section 2.2 Closing.
Subject to the terms and conditions hereof, the consummation of the purchase and sale of the Purchased Units hereunder (the “Closing”) shall take place at the offices of Perkins Coie LLP, 1120 N.W. Couch Street, Portland, Oregon
97209-4128, or such other location as mutually agreed by the parties and upon the satisfaction or waiver of the conditions set forth in Sections 2.3, 2.4 and 2.5 (the date of such closing, the “Closing Date”). 

  
 5 

 Section 2.3 Mutual Conditions. The respective obligations of each
party to consummate the purchase and issuance and sale of the Purchased Units shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions (any or all of which may be waived by a party on behalf of itself
in writing, in whole or in part, to the extent permitted by applicable Law): 
 (a) No Law shall have been enacted or
promulgated, and no action shall have been taken, by any Governmental Authority of competent jurisdiction that temporarily, preliminarily or permanently restrains, precludes, enjoins or otherwise prohibits the consummation of the transactions
contemplated by the Operative Documents or makes the transactions contemplated hereby illegal; 
 (b) There shall not be
pending any suit, action or proceeding by any Governmental Authority seeking to restrain, preclude, enjoin or prohibit the transactions contemplated by the Operative Documents; 

(c) The sum of (a) the aggregate Purchase Prices of the Purchasers paid for Purchased Units at the Closing and
(b) the aggregate purchase price of investors purchasing Series D Preferred Units as part of the Series D Offering shall equal or exceed $200 million; and 

(d) The consent required to approve the Partnership’s proposed bond amendment has been obtained, and all conditions
precedent to the Partnership’s proposed bond amendment shall have been completed, on terms not materially different from those distributed to the Partnership’s bondholders on May 19, 2016 and without waiver of any conditions precedent
set forth therein other than with respect to the composition of the equity securities (preferred or common) to be sold by the Partnership. 

Section 2.4 Each Purchaser’s Conditions. The obligation of each Purchaser to consummate the purchase of its
Purchased Units shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions (any or all of which may be waived by a particular Purchaser on behalf of itself in writing with respect to its Purchased Units,
in whole or in part, to the extent permitted by applicable Law): 
 (a) The Partnership shall have performed and complied
with the covenants and agreements contained in this Agreement that are required to be performed and complied with by the Partnership on or prior to the Closing Date; 

(b) (i) The representations and warranties of the Partnership contained in this Agreement that are qualified by
materiality or a Material Adverse Effect shall be true and correct when made and as of the Closing Date as if made on and as of the Closing Date (except that any such representations and warranties made as of a specific date shall be required to be
true and correct as of such date only) and (ii) all other representations and warranties of the Partnership contained in this Agreement shall be true and correct in all material respects when made and as of the Closing Date as if made on and as
of the Closing Date (except that any such representations and warranties made as of a specific date shall be required to be true and correct in all material respects as of such date only); 

  
 6 

 (c) The Partnership shall have delivered, or caused to be delivered, to the
Purchasers at the Closing, the Partnership’s closing deliveries described in Section 2.6; 
 (d) The
Partnership shall have filed a supplemental listing application with the NYSE to list the Purchased Units; 
 (e) No notice
of delisting from the NYSE shall have been received by the Partnership with respect to the Common Units; 
 (f) The Common
Units shall not have been suspended by the Commission or the NYSE from trading on the NYSE nor shall suspension by the Commission or the NYSE have been threatened in writing by the Commission or the NYSE; and 

(g) Since the date of this Agreement, no Material Adverse Effect shall have occurred and be continuing. 

Section 2.5 The Partnership’s Conditions. The obligation of the Partnership to consummate the sale of the
Purchased Units to a Purchaser shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions with respect to such Purchaser (any or all of which may be waived by the Partnership in writing, in whole or in
part, to the extent permitted by applicable Law): 
 (a) (i) The representations and warranties of such Purchaser contained
in this Agreement that are qualified by materiality shall be true and correct when made and as of the Closing Date (except that any such representations and warranties made as of a specific date shall be required to be true and correct as of such
date only) and (ii) all other representations and warranties of such Purchaser contained in this Agreement shall be true and correct in all material respects when made and as of the Closing Date (except that any such representations of such
Purchaser made as of a specific date shall be required to be true and correct in all material respects as of such date only); and 

(b) Such Purchaser shall have delivered, or caused to be delivered, to the Partnership at the Closing such Purchaser’s
closing deliveries described in Section 2.7. 
 By acceptance of the applicable Purchased Units, each Purchaser
shall be deemed to have represented to the Partnership that such Purchaser has performed and complied in all material respects with the covenants and agreements contained in this Agreement that are required to be performed and complied with by it on
or prior to the Closing Date; and the representations and warranties of such Purchaser contained in this Agreement that are qualified by materiality are true and correct as of the Closing Date (except that any such representations and warranties
made as of a specific date shall be required to be true and correct as of such date only) and all other representations and warranties of such Purchaser are true and correct in all material respects as of the Closing Date (except that any such
representations and warranties made as of a specific date shall be required to be true and correct in all material respects as of such date only). 

  
 7 

 Section 2.6 Partnership Deliveries. At the Closing, subject to the
terms and conditions hereof, the Partnership will deliver, or cause to be delivered, to each Purchaser: 
 (a) At the
election of each Purchaser, either (i) evidence of issuance of the Purchased Units purchased by each Purchaser credited to book-entry accounts maintained by the transfer agent, or (ii) physical certificates representing the Purchased Units
purchased by such Purchaser, duly executed on behalf of the Partnership and registered in the name of such Purchaser (or its nominee) (which physical certificates shall be delivered in .pdf format on the Closing Date and promptly mailed to the
address specified by such Purchaser), in each case, bearing a restrictive notation free and clear of any Liens, other than under applicable federal and state securities laws, it being understood that such Purchased Shares shall be issued only after
receipt by the Partnership of the full Unit Price therefor; 
 (b) A countersigned “Supplemental Listing
Application” approving the Common Units for listing by the NYSE, subject to notice of issuance; 
 (c) Copies of
(i) the Certificate of Limited Partnership of the Partnership and (ii) the Certificate of Formation of the General Partner, each certified by the Registrar of Corporations of the Republic of the Marshall Islands as of a recent date; 

(d) A certificate of the Registrar of Corporations of the Republic of the Marshall Islands, dated a recent date, to the effect
that each of the General Partner and the Partnership is in good standing; 
 (e) A cross-receipt executed by the Partnership
and delivered to such Purchaser certifying that it has received the Purchase Price from such Purchaser as of the Closing Date; 

(f) An opinion addressed to the Purchasers from Perkins Coie LLP, legal counsel to the Partnership, dated as of the Closing
Date, in the form and substance attached hereto as Exhibit B; 
 (g) An opinion addressed to the Purchasers from
Watson Farley & Williams LLP, relating to Marshall Islands law, dated as of the Closing Date, in the form and substance attached hereto as Exhibit C; 

(h) A certificate, dated the Closing Date and signed by the Chief Executive Officer and by the Chief Financial Officer, any
Vice President or Secretary of the General Partner, on behalf of the Partnership, in his or her capacities as such, stating that: 

(i) The Partnership has performed and complied with the covenants and agreements contained in this Agreement
that are required to be performed and complied with by the Partnership on or prior to the Closing Date; and 

(ii) The representations and warranties of the Partnership contained in this Agreement that are qualified by
materiality or Material Adverse Effect were true and correct when made and are true and correct as of the Closing Date and all other representations and warranties of the Partnership were true and correct in all material respects when made and are
true and correct in all material respects as of the Closing Date; in each case as though made at and as of the Closing Date (except that representations and warranties made as of a specific date shall be required to be true and correct or true and
correct in all material respects, as applicable, as of such date only); and 

  
 8 

 (i) A certificate of the Secretary or Assistant Secretary of the General Partner,
on behalf of the Partnership, certifying as to (1) the Certificate of Limited Partnership of the Partnership and the Partnership Agreement and the Restated Partnership Agreement, (2) the Certificate of Formation of the General Partner and
its Limited Liability Company Agreement, (3) board resolutions authorizing the execution and delivery of the Operative Documents and the consummation of the transactions contemplated thereby, including the issuance of the Purchased Units and
(4) the signatures of the officers executing the Operative Documents; and 
 (j) the Registration Rights Agreement,
which shall have been duly executed by the Company. 
 Section 2.7 Purchaser Deliveries. At the Closing,
subject to the terms and conditions hereof, each Purchaser will deliver, or cause to be delivered, to the Partnership: 

(a) Payment to the Partnership of the Purchase Price set forth opposite such Purchaser’s name under the column titled
“Purchase Price” on Schedule A hereto by wire transfer of immediately available funds to an account designated by the Partnership in writing at least two Business Days prior to the Closing Date; provided, however, that
such delivery shall only be required after the delivery of the Purchased Units as set forth in Section 2.6(a); and 

(b) A cross-receipt executed by such Purchaser and delivered to the Partnership certifying that it has received its Purchased
Units as of the Closing Date. 
 (c) the Registration Rights Agreement, duly executed by such Purchaser. 

Section 2.8 Independent Nature of Purchasers’ Obligations and Rights. The obligations of each Purchaser
under this Agreement are several and not joint with the obligations of any other Purchaser, and no Purchaser shall be responsible in any way for the performance of the obligations of any other Purchaser under this Agreement. Nothing contained
herein, and no action taken by any Purchaser pursuant hereto, shall be deemed to constitute the Purchasers as a partnership, an association, a joint venture or any other kind of group or entity, or create a presumption that the Purchasers are in any
way acting in concert or as a group with respect to such obligations or the transactions contemplated by this Agreement. Each Purchaser shall be entitled to independently protect and enforce its rights, including the rights arising out of this
Agreement, and it shall not be necessary for any other Purchaser to be joined as an additional party in any proceeding for such purpose. It is expressly understood and agreed that each provision contained in this Agreement is between the Partnership
and a Purchaser, solely, and not between the Partnership and the Purchasers collectively and not between and among the Purchasers. 

  
 9 

 ARTICLE III 

REPRESENTATIONS AND WARRANTIES OF THE PARTNERSHIP 

The Partnership represents and warrants to each Purchaser as follows: 

Section 3.1 Existence. Each of the Partnership Entities has been duly incorporated or formed, as the case may be,
and is validly existing as a limited liability company, limited partnership or corporation, as the case may be, in good standing under the Laws of its jurisdiction of incorporation or formation, as the case may be, and has the full limited liability
company, limited partnership or corporate, as the case may be, power and authority, and has all governmental licenses, authorizations, consents and approvals, necessary to own, lease or hold its Properties and assets and to conduct the businesses in
which it is engaged, and is duly registered or qualified to do business and in good standing as a foreign limited liability company, limited partnership or corporation, as the case may be, in each jurisdiction in which its ownership or lease of
Property or the conduct of its business requires such qualification, except where the failure to so register or qualify would not reasonably be expected to (i) have, individually or in the aggregate, a material adverse effect on the condition
(financial or other), results of operations, securityholders’ equity, Properties, business, assets or prospects of the Partnership Entities taken as a whole, the ability of the Partnership Entities to meet their obligations under the Operative
Documents or the ability of the Partnership Entities to consummate the transactions under any Operative Document on a timely basis (except, in each case, to the extent any such material adverse effect after the date hereof results from, arises out
of or relates to: (A) the announcement of the transactions contemplated by this Agreement or the satisfaction of the obligations set forth herein, (B) a general deterioration in the economy or changes in the general state of the industries
in which the Partnership Entities operate, except to the extent that the Partnership Entities, taken as a whole, are adversely affected in a disproportionate manner as compared to other industry participants, (C) the outbreak or escalation of
hostilities involving the United States, the declaration by the United States of a national emergency or war or the occurrence of any other calamity or crisis, including acts of terrorism, or (D) changes in accounting principles or regulations
imposed upon the Partnership Entities or their businesses applicable generally or to such industries (a “Material Adverse Effect”)) or (ii) subject the limited partners of the Partnership to any material liability or
disability. 
 Section 3.2 Purchased Units; Capitalization.  

(a) On the Closing Date, the Purchased Units shall have those rights, preferences, privileges and restrictions governing the
Common Units as set forth in the Restated Partnership Agreement, which shall be unchanged with respect to such rights, preferences, privileges and restrictions from those in the Partnership Agreement. 

(b) The General Partner is the sole general partner of the Partnership, with a 2.0% general partner interest in the Partnership
(not including any Preferred Units); such general partner interest is the only general partner interest of the Partnership that is issued and outstanding; and such general partner interest has been duly authorized and validly issued and is owned by
the General Partner free and clear of any Liens (except restrictions on transferability contained in the Restated Partnership Agreement). 

  
 10 

 (c) As of the date of this Agreement, prior to the issuance and sale of the
Purchased Units, as contemplated hereby, the issued and outstanding limited partner interests of the Partnership consist of (i) 107,128,349 Common Units, (ii) 6,000,000 of the Partnership’s 7.25% Series A Cumulative Redeemable
Preferred Units (“Series A Preferred Units”), (iii) 5,000,000 of the Partnership’s 8.50% Series B Cumulative Redeemable Preferred Units (“Series B Preferred Units”), (iv) 10,438,413 of the
Partnership’s 8.60% Series C Cumulative Convertible Perpetual Preferred Units (“Series C Preferred Units”), and (v) the Incentive Distribution Rights (as defined in the Partnership Agreement and the Restated
Partnership Agreement). All outstanding Common Units, Preferred Units and Incentive Distribution Rights and the limited partner interests represented thereby have been duly authorized and validly issued in accordance with the Partnership Agreement
or the Restated Partnership Agreement and are fully paid (to the extent required under the Partnership Agreement and the Restated Partnership Agreement) and nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60
of the Marshall Islands LP Act and the Partnership Agreement and Restated Partnership Agreement). Prior to the Closing, the Partnership intends to adopt the Restated Partnership Agreement which will also, among other things, set forth the rights,
preferences, privileges and restrictions governing the Partnership’s Series C-1 Preferred Units and the Partnership’s Series D Preferred Units (the Series C-1 Preferred Units and the Series D Preferred Units, together with the
Series A Preferred Units, the Series B Preferred Units, the Series C Preferred Units, collectively the “Preferred Units”) to be issued as part of the Partnership’s recapitalization plan. In connection with the
Series C Transaction, at or about the time of the Closing, the Partnership will exchange 1,920,668 Series C Preferred Units for 8,323,809 Common Units, and the remaining 8,517,745 Series C Preferred Units will be exchanged on a one-for-one basis
into Series C-1 Preferred Unit. In connection with the Series D Offering, at or about the time of the Closing, the Partnership will issue up to $200 million of Series D Preferred Units at a price of $25.00 per Series D Preferred Unit. For each
Series D Preferred Unit purchased, the purchaser will receive two Series D Warrants, one warrant to purchase 1.125 Common Units, and a second warrant to purchase 0.5625 Common Unit. 

(d) The Common Units are listed on the NYSE, and the Partnership has not received any notice of delisting. 

(e) The Common Units are, and the Purchased Units will be upon issuance, “covered securities” for purposes of
Section 18 of the Securities Act. 
 Section 3.3 Subsidiaries. 

(a) The Partnership owns a 100% membership interest in Teekay Offshore Holdings L.L.C., a Marshall Islands limited liability
company (“Teekay Offshore Holdings”); such membership interest has been duly authorized and validly issued in accordance with the limited liability company agreement of Teekay Offshore Holdings, as amended on or prior to the date
hereof (the “Teekay Offshore Holdings LLC Agreement”), and is fully paid (to the extent required under the Teekay Offshore Holdings LLC Agreement) and nonassessable (except as such nonassessability may be affected by Sections 20,
31, 40 and 49 of the Marshall Islands LLC Act and except as may be provided in the Teekay Offshore Holdings LLC Agreement); and the Partnership owns such membership interest free and clear of all Liens except for Liens pursuant to credit agreements
and related security agreements disclosed or referred to in the Partnership SEC Documents. 

  
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 (b) Teekay Offshore Holdings owns a 100% membership interest in OLP GP; such
membership interest has been duly authorized and validly issued in accordance with the limited liability company agreement of OLP GP, as amended or restated on or prior to the date hereof (the “OLP GP LLC Agreement”), and is fully
paid (to the extent required under the OLP GP LLC Agreement) and nonassessable (except as such nonassessability may be affected by Sections 20, 31, 40 and 49 of the Marshall Islands LLC Act and the organizational documents of OLP GP); and Teekay
Offshore Holdings owns such membership interest free and clear of all Liens except for Liens pursuant to credit agreements and related security agreements disclosed or referred to in the Partnership SEC Documents. 

(c) Teekay Offshore Holdings directly owns a 99.09% limited partner interest in the Operating Company and OLP GP directly owns
a 0.91% general partner interest in the Operating Company; such partner interests have been duly authorized and validly issued in accordance with the partnership agreement of the Operating Company, as amended or restated on or prior to the date
hereof (the “Operating Company Partnership Agreement”), and are fully paid (to the extent required under such Operating Company Partnership Agreement) and, with respect to the limited partner interests, are nonassessable (except as
such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and the organizational documents of the Operating Company); and Teekay Offshore Holdings and OLP GP, respectively, own such partner interests free and
clear of all Liens except for Liens pursuant to credit agreements and related security agreements disclosed or referred to in the Partnership SEC Documents. 

(d) The Partnership and the Operating Company own, directly or indirectly, the equity interests indicated in such Exhibit of
the Subsidiaries described in Exhibit 8.1 to the Partnership’s Annual Report on Form 20-F for the year ended December 31, 2015; such equity interests have been duly authorized and validly issued in accordance with the organizational
documents of each Subsidiary, and are fully paid (to the extent required under such organizational documents) and nonassessable (except as such nonassessability may be affected by the applicable statutes of the jurisdiction of formation of the
applicable Subsidiary and the relevant organizational documents); and the Partnership and the Operating Company, as applicable, own such equity interests free and clear of all Liens except for Liens pursuant to credit agreements and related security
agreements disclosed or referred to in the Partnership SEC Documents. 

  
 12 

 Section 3.4 No Conflict. None of (i) the offering, issuance and
sale by the Partnership of the Purchased Units and the application of the proceeds therefrom, (ii) the execution, delivery and performance of the Operative Documents by the Partnership, or (iii) the consummation of the transactions
contemplated hereby or thereby conflicts or will conflict with, or results or will result in a breach or violation of or imposition of any Lien upon any Property or assets of the Partnership Entities pursuant to, (A) the formation or governing
documents of any of the Partnership Entities, (B) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which any of the
Partnership Entities is a party, by which any of them is bound or to which any of their respective Properties or assets is subject, or (C) any Law applicable to any of the Partnership Entities or injunction of any court or governmental agency
or body to which any of the Partnership Entities of any court, regulatory body, administrative agency, governmental body, arbitrator or other authority having jurisdiction over any of the Partnership Entities or any of their Properties, except in
the case of clause (B) for such conflict, breach, violation or default that would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

Section 3.5 No Default. None of the Partnership Entities is in violation or default of (i) any provision of
its respective formation or governing documents, (ii) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which it is a party,
by which it is bound or to which its property is subject, or (iii) any Law of any court, regulatory body, administrative agency, governmental body, arbitrator or other authority having jurisdiction over the Partnership Entities or any of their
Properties, as applicable, except, in the case of clauses (ii) or (iii), as would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

Section 3.6 Authority. The Partnership has all requisite power and authority to enter into this Agreement. On the
Closing Date, the Partnership will have all requisite power and authority to issue, sell and deliver the Purchased Units, in accordance with and upon the terms and conditions set forth in this Agreement and the Restated Partnership Agreement. On the
Closing Date, all partnership or limited liability company action, as the case may be, required to be taken by the General Partner and the Partnership for the authorization, issuance, sale and delivery of the Purchased Units, the execution and
delivery of the Operative Documents and the consummation of the transactions contemplated hereby and thereby shall have been validly taken. No approval from the holders of outstanding Common Units is required under the Partnership Agreement or will
be required under the Restated Partnership Agreement or the rules of the NYSE in connection with the Partnership’s issuance and sale of the Purchased Units to the Purchasers. 

Section 3.7 Approvals. Except as required by the Commission in connection with the Partnership’s obligations
under the Registration Rights Agreement, no authorization, consent, approval, waiver, license, qualification or written exemption from, nor any filing, declaration, qualification or registration with, any Governmental Authority or any other Person
is required in connection with the execution, delivery or performance by the Partnership of any of the Operative Documents to which it is a party or the Partnership’s issuance and sale of the Purchased Units, except as may be required under the
state securities or “Blue Sky” Laws. 

  
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 Section 3.8 Compliance with Laws. Neither the Partnership nor any of
its Subsidiaries is in violation of any Law applicable to the Partnership or its Subsidiaries, except as would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. The Partnership and its Subsidiaries
possess all certificates, authorizations and permits issued by the appropriate regulatory authorities necessary to conduct their respective businesses, except where the failure to possess such certificates, authorizations or permits would not
reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect, and neither the Partnership nor any such Subsidiary has received any notice of proceedings relating to the revocation or modification of any such
certificate, authorization or permit, except where such potential revocation or modification would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

Section 3.9 Due Authorization. Each of the Operative Documents has been duly and validly authorized and has been,
or with respect to the Operative Documents to be delivered at the Closing Date, will be, validly executed and delivered by the Partnership or the General Partner, as the case may be, and constitutes, or will constitute, the legal, valid and binding
obligations of the Partnership or the General Partner, as the case may be, enforceable in accordance with its terms, except as such enforceability may be limited by bankruptcy, insolvency, reorganization and other laws of general applicability
relating to or affecting creditors’ rights and by general principles of equity, including principles of commercial reasonableness, fair dealing and good faith. 

Section 3.10 Valid Issuance; No Options or Preemptive Rights; Title. The Purchased Units to be issued and sold by
the Partnership to each Purchaser hereunder have been duly authorized in accordance with the Partnership Agreement and, when issued and delivered against payment therefor pursuant to this Agreement, will be validly issued in accordance with the
Restated Partnership Agreement, fully paid (to the extent required under the Restated Partnership Agreement) and non-assessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and the
Restated Partnership Agreement) and will be free of any and all Liens and restrictions on transfer, other than (i) restrictions on transfer under the Restated Partnership Agreement or this Agreement and under applicable federal and state
securities laws and (ii) such Liens as are created by the Purchasers. Except as set forth in the Partnership Agreement with respect to the General Partner, the holders of outstanding Common Units are not entitled to statutory, preemptive or
other similar contractual rights to subscribe for Common Units; and, except for the Series D Warrants, the Series C Transaction and as set forth in the Restated Partnership Agreement, no options, warrants or other rights to purchase, agreements or
other obligations to issue, or rights to convert any obligations into or exchange any securities for, partnership securities or ownership interests in the Partnership are outstanding. 

Section 3.11 No Registration Rights. Except as contemplated by the Partnership Agreement, this Agreement, the
Registration Rights Agreement, the Series D Registration Rights Agreement, and the Existing Registration Rights Agreement, there are no contracts, agreements or understandings between the Partnership and any Person granting such Person the right to
require the Partnership to file a registration statement under the Securities Act with respect to any securities of the Partnership or to require the Partnership to include such securities in any securities registered or to be registered pursuant to
any registration statement filed by or required to be filed by the Partnership under the Securities Act. 

  
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 Section 3.12 Periodic Reports. The Partnership’s forms,
registration statements, reports, schedules and statements required to be filed by it under the Exchange Act or the Securities Act (all such documents filed prior to the date hereof, collectively the “Partnership SEC Documents”)
have been filed with the Commission on a timely basis. The Partnership SEC Documents, including any audited or unaudited financial statements and any notes thereto or schedules included therein, at the time filed (or in the case of registration
statements, solely on the dates of effectiveness) (except to the extent corrected by a subsequent Partnership SEC Document) (a) did not contain any untrue statement of a material fact or omit to state a material fact required to be stated
therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading, (b) complied in all material respects with the applicable requirements of the Exchange Act and the
Securities Act, as the case may be, (c) in the case of the financial statements, complied as to form in all material respects with applicable accounting requirements and with the published rules and regulations of the Commission with respect
thereto, (d) in the case of the financial statements, were prepared in accordance with GAAP applied on a consistent basis during the periods involved (except as may be indicated in the notes thereto or, in the case of unaudited statements, for
the absence of certain footnote disclosure and normal, recurring year-end adjustments or as otherwise permitted by the rules and regulations of the Commission), and (e) fairly present (subject in the case of unaudited statements to normal and
recurring audit adjustments) in all material respects the consolidated financial position of the Partnership and its consolidated subsidiaries as of the dates thereof and the consolidated results of its operations and cash flows for the periods then
ended. KPMG LLP is an independent registered public accounting firm with respect to the Partnership and the General Partner and has not resigned or been dismissed as independent registered public accountants of the Partnership as a result of or in
connection with any disagreement with the Partnership on any matter of accounting principles or practices, financial statement disclosure or auditing scope or procedures. 

Section 3.13 Litigation. As of the date hereof, except as set forth on Schedule 3.13 hereto or in the
Partnership’s Annual Report on Form 20-F for the year ended December 31, 2015, there are no legal or governmental proceedings pending to which any Partnership Entity is a party or to which any Property or asset of any Partnership Entity is
subject that could reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect or which challenges the validity of any of the Operative Documents or the right of any Partnership Entity to enter into any of the
Operative Documents or to consummate the transactions contemplated hereby and thereby and, to the knowledge of the Partnership, no such proceedings are threatened by Governmental Authorities or others. 

Section 3.14 Insurance. The Partnership and its Subsidiaries are insured by insurers of recognized financial
responsibility against such losses and risks and in such amounts as are prudent and customary in the businesses in which they are engaged. The Partnership does not have any reason to believe that it or any Subsidiary will not be able to renew its
existing insurance coverage as and when such coverage expires or to obtain similar coverage from similar insurers as may be necessary to continue its business. 

Section 3.15 Internal Accounting Controls. The Partnership and its Subsidiaries maintain a system of internal
accounting controls sufficient to provide reasonable assurance that (i) transactions are executed in accordance with management’s general or specific authorizations, (ii) transactions are recorded as necessary to permit preparation of
financial statements in conformity with GAAP and to maintain asset accountability, (iii) access to assets is permitted only in accordance with management’s general or specific authorization, and (iv) the recorded accountability for
assets is compared with the existing assets at reasonable intervals and appropriate action is taken with respect to any differences. The Partnership is not aware of any failures of such internal accounting controls. 

  
 15 

 Section 3.16 No Material Adverse Change. As of the date hereof,
except as set forth in the Partnership’s Report on Form 6-K for the quarter ended March 31, 2016, since March 31, 2016, there has been no change, event, occurrence, effect, fact, circumstance or condition that has had or would
reasonably be likely to have a Material Adverse Effect. 
 Section 3.17 Certain Fees. Other than fees payable
to Citigroup Global Markets, Inc. and DNB Markets, Inc. for their services as placement agents, no fees or commissions are or will be payable by the Partnership to brokers, finders, or investment bankers with respect to the sale of any of the
Purchased Units or the consummation of the transactions contemplated by this Agreement. 
 Section 3.18 No Side
Agreements. There are no agreements by, among or between the Partnership or any of its Affiliates, on the one hand, and any Purchaser or any of their Affiliates, on the other hand, with respect to the transactions contemplated hereby other than
the Operative Documents and agreements entered into in connection with the Series C Transaction and the Series D Offering, nor promises or inducements for future transactions between or among any of such parties. 

Section 3.19 No Registration. Assuming the accuracy of the representations and warranties of each Purchaser
contained in Article IV, the issuance and sale of the Purchased Units pursuant to this Agreement is exempt from registration requirements of the Securities Act, and neither the Partnership nor, to the knowledge of the Partnership, any authorized
Representative acting on its behalf has taken or will take any action hereafter that would cause the loss of such exemption. 

Section 3.20 Investment Company Status. The Partnership is not required to be registered as an “investment
company” under the Investment Company Act of 1940, as amended. 
 Section 3.21 Form F-3 Eligibility. As of
the date hereof, the Partnership has been, since the time of filing its most recent registration statement on Form F-3, and continues to be eligible to use Form F-3. 

Section 3.22 Passive Foreign Investment Company. To the knowledge of the Partnership, after consultation with
United States federal income tax counsel, none of the Partnership Entities is a Passive Foreign Investment Company within the meaning of Section 1297 of the Internal Revenue Code of 1986, as amended. 

Section 3.23 Tax Status. None of the Partnership Entities, other than the Partnership and the General Partner,
has elected to be classified as an association taxable as a corporation for United States federal income tax purposes. Each of the Partnership Entities, other than the Partnership and the General Partner, is, or will pursuant to Treasury Regulations
Section 301.7701-3 timely and properly elect to be, classified as a disregarded entity if it has one owner or as a partnership if it has more than one owner for United States federal income tax purposes. 

  
 16 

 Section 3.24 Foreign Corrupt Practices Act. No Partnership Entity,
nor any director, officer, or employee, nor, to the knowledge of the Partnership Entities, any agent or representative of the Partnership Entities, has taken or will take any action, directly or indirectly, that would result in a violation by such
persons of the Foreign Corrupt Practices Act of 1977, as amended (such act, including the rules and regulations thereunder, the “FCPA”), including, making use of the mails or any means or instrumentality of interstate commerce
corruptly in furtherance of an offer, payment, promise to pay, or authorization or approval of the payment or giving of money, property, gifts or anything else of value, directly or indirectly, to any “government official” (including any
officer or employee of a government or government-owned or controlled entity or of a public international organization, or any person acting in an official capacity for or on behalf of any of the foregoing, or any political party or party official
or candidate for political office) to influence official action or secure an improper advantage; and the Partnership Entities have conducted their businesses in compliance with applicable anti-corruption laws and have instituted and maintain and
will continue to maintain policies and procedures designed to promote and achieve compliance with such laws and with the representation and warranty contained herein. 

ARTICLE IV 

REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS 

Each Purchaser, severally and not jointly, hereby represents and warrants to the Partnership that: 

Section 4.1 Existence. Such Purchaser is duly organized and validly existing and in good standing under the Laws
of its jurisdiction of organization, with all requisite power and authority to own, lease, use and operate its Properties and to conduct its business as currently conducted. 

Section 4.2 Authorization, Enforceability. Such Purchaser has all necessary corporate, limited liability company
or partnership power and authority to execute, deliver and perform its obligations under the Operative Documents and to consummate the transactions contemplated thereby, and the execution, delivery and performance by such Purchaser of The Operative
Documents has been duly authorized by all necessary action on the part of such Purchaser; and this Agreement, and the Registration Rights Agreement, when delivered at the Closing will, constitute the legal, valid and binding obligations of such
Purchaser, enforceable in accordance with their respective terms, except as such enforceability may be limited by bankruptcy, insolvency, fraudulent transfer and similar laws affecting creditors’ rights generally or by general principles of
equity, including principles of commercial reasonableness, fair dealing and good faith. 

  
 17 

 Section 4.3 No Breach. The execution, delivery and performance of
the Operative Documents by such Purchaser and the consummation by such Purchaser of the transactions contemplated thereby will not (a) conflict with or result in a breach or violation of any of the terms or provisions of, or constitute a
default under, any material agreement to which such Purchaser is a party or by which such Purchaser is bound or to which any of the Property or assets of such Purchaser is subject, (b) conflict with or result in any violation of the provisions
of the organizational documents of such Purchaser, or (c) violate any statute, order, rule or regulation of any court or governmental agency or body having jurisdiction over such Purchaser or the property or assets of such Purchaser, except in
the cases of clauses (a) and (c), for such conflicts, breaches, violations or defaults as would not prevent the consummation of the transactions contemplated by the Operative Documents. 

Section 4.4 Certain Fees. No fees or commissions are or will be payable by such Purchaser to brokers, finders, or
investment bankers with respect to the purchase of any of the Purchased Units or the consummation of the transaction contemplated by this Agreement. 

Section 4.5 No Side Agreements. There are no other agreements by, among or between such Purchaser and any of its
Affiliates, on the one hand, and the Partnership or any of its Affiliates, on the other hand, with respect to the transactions contemplated hereby other than the Operative Documents and agreements entered into in connection with the Series D
Offering and the Series C Transaction nor promises or inducements for future transactions between or among any of such parties; provided, however, that, subject to such Purchaser’s compliance with its obligations under the U.S. federal
securities laws and its internal policies: (a) such Purchaser, for purposes hereof, shall not be deemed to include any employees, subsidiaries or Affiliates that are effectively walled off by appropriate “Chinese Wall” information
barriers approved by such Purchaser’s legal or compliance department (and thus have not been privy to any information concerning this transaction) (a “Walled Off Person”) and (b) the foregoing representations in this
paragraph shall not apply to any transaction by or on behalf of such Purchaser that was effected by a Walled Off Person in the ordinary course of trading without the advice or participation of such Purchaser or receipt of confidential or other
information regarding this transaction provided by such Purchaser to such entity. 
 Section 4.6 Investment.
The Purchased Units are being acquired for such Purchaser’s own account, the account of its Affiliates, or the accounts of clients for whom such Purchaser exercises discretionary investment authority (all of whom such Purchaser hereby
represents and warrants are “accredited investors” within the meaning of Rule 501(a) of Regulation D promulgated by the Commission pursuant to the Securities Act), not as a nominee or agent, and with no present intention of distributing
the Purchased Units or any part thereof, and such Purchaser has no present intention of selling or granting any participation in or otherwise distributing the same in any transaction in violation of the securities laws of the United States or other
jurisdiction, without prejudice, however, to such Purchaser’s right at all times to sell or otherwise dispose of all or any part of the Purchased Units under a registration statement under the Securities Act and applicable state securities laws
or under an exemption from such registration available thereunder (including, without limitation, if available, Rule 144 promulgated thereunder). If such Purchaser should in the future decide to dispose of any of the Purchased Units, such
Purchaser understands and agrees (a) that it may do so only in compliance with the Securities Act and applicable state or other securities law, as then in effect, including a sale contemplated by any registration statement pursuant to which
such securities are being offered, or pursuant to an exemption from the Securities Act, and (b) that stop-transfer instructions to that effect will be in effect with respect to such securities. 

  
 18 

 Section 4.7 Nature of Purchaser. Such Purchaser represents and
warrants to, and covenants and agrees with, the Partnership that, (a) it is an “accredited investor” within the meaning of Rule 501 of Regulation D promulgated by the Commission pursuant to the Securities Act and (b) by reason of
its business and financial experience it has such knowledge, sophistication and experience in making similar investments and in business and financial matters generally so as to be capable of evaluating the merits and risks of the prospective
investment in the Purchased Units, is able to bear the economic risk of such investment and, at the present time, would be able to afford a complete loss of such investment. 

Section 4.8 Restricted Securities. Such Purchaser understands that the Purchased Units are characterized as
“restricted securities” under the federal securities Laws inasmuch as they are being acquired from the Partnership in a transaction not involving a public offering and that under such Laws and applicable regulations such securities may be
resold without registration under the Securities Act only in certain limited circumstances. In this connection, such Purchaser represents that it is knowledgeable with respect to Rule 144 of the Commission promulgated under the Securities Act. 

Section 4.9 Legend. Such Purchaser understands that any certificates evidencing the Purchased Units will bear the
legend required by the Partnership Agreement as well as the following legend: “THE UNITS EVIDENCED BY THIS ADVICE HAVE NOT BEEN REGISTERED UNDER THE U.S. SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR ANY OTHER
SECURITIES LAWS AND MAY NOT BE SOLD, PLEDGED OR OTHERWISE TRANSFERRED EXCEPT IN ACCORDANCE WITH THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT, OR AN EXEMPTION THEREFROM AND, IN EACH CASE, IN COMPLIANCE WITH APPLICABLE SECURITIES LAWS.”
Purchased Units held in book-entry accounts shall bear a notation of such restrictive legend. 
 Section 4.10 Short
Selling. Such Purchaser has not made any trades in the Common Units, Preferred Units or any other equity interests of the Partnership or entered into or effected any Short Sales of the Common Units owned by it between (a) the earlier of
(x) the time it first began discussion with the Partnership about the transactions contemplated by this Agreement and (y) Friday, June 10, 2016 and (b) the date hereof (it being understood that, without implication that the
contrary would otherwise be true, the entering into of a total return swap shall not be considered a Short Sale of Common Units); provided, however, that, subject to such Purchaser’s compliance with its obligations under the U.S. federal
securities laws and its internal policies: (a) such Purchaser, for purposes hereof, shall not be deemed to include any Walled Off Person and (b) the foregoing representations in this paragraph shall not apply to any transaction by or on
behalf of Purchaser that was effected by a Walled Off Person in the ordinary course of trading without the advice or participation of Purchaser or receipt of confidential or other information regarding this transaction provided by Purchaser to such
entity. 

  
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 Section 4.11 Trading Activities. Such Purchaser’s trading
activities, if any, with respect to the Common Units will be in compliance with all applicable state and federal securities laws, rules and regulations and the rules and regulations of the NYSE. 

Section 4.12 Short Selling Acknowledgement and Agreement. Each Purchaser understands and acknowledges, severally
and not jointly with any other Purchaser, that the Commission currently takes the position that coverage of short sales of securities “against the box” prior to the effective date of a registration statement or prior to the time a
Purchaser is eligible to sell such securities under Rule 144 is a violation of Section 5 of the Securities Act. 

Section 4.13 Purchaser Investigation; Partnership Projections. Such Purchaser acknowledges and agrees that it has
made its own inquiry and investigation into, and, based thereon, has formed an independent judgment concerning the Partnership and its businesses and operations and prospects, and such Purchaser has been furnished with or given full access to such
information about the Partnership and its businesses and operations as it requested. In connection with such Purchaser’s investigation of the Partnership and its businesses and operations, such Purchaser and its Representatives have received
from the Partnership or its Representatives certain projections and other forecasts for the Partnership and certain estimates, plans and budget information. Such Purchaser acknowledges and agrees that (a) there are uncertainties inherent in
attempting to make such projections, forecasts, estimates, plans and budgets, (b) such Purchaser is familiar with such uncertainties and (c) such Purchaser is taking full responsibility for making its own evaluations of the adequacy and
accuracy of all estimates, projections, forecasts, plans and budgets so furnished to it or its Representatives. 
 ARTICLE V 

COVENANTS 

Section 5.1 Taking of Necessary Action. Each of the parties hereto shall use its commercially reasonable efforts
promptly to take or cause to be taken all action and promptly to do or cause to be done all things necessary, proper or advisable under applicable Law and regulations to consummate and make effective the transactions contemplated by this Agreement.
Without limiting the foregoing, the Partnership and each Purchaser shall use its commercially reasonable efforts to make all filings and obtain all consents of Governmental Authorities that may be necessary or, in the reasonable opinion of the other
parties, as the case may be, advisable for the consummation of the transactions contemplated by the Operative Documents. 

Section 5.2 Other Actions. The Partnership shall, prior to the Closing, file a supplemental listing application
with the NYSE to list the Purchased Units. 
 Section 5.3 Payment and Expenses. The Partnership and each
Purchaser shall be responsible for its own fees and expenses in connection with the transactions contemplated by this Agreement. 

  
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 Section 5.4 Use of Proceeds. The Partnership shall use the
collective proceeds from the sale of the Purchased Units fund growth capital expenditures, reduce indebtedness of the Partnership senior to the Preferred Units, and other general partnership purposes. 

Section 5.5 Delivery of Purchased Units. Prior to and following the Closing, the Partnership shall, and shall
cause its transfer agent to, reasonably cooperate with each Purchaser to ensure that the Purchased Units are validly and effectively issued to such Purchaser and that such Purchaser’s ownership of the Purchased Units following the Closing is
accurately reflected on the appropriate books and records of the Partnership’s transfer agent. 
 ARTICLE VI 

INDEMNIFICATION 

Section 6.1 Indemnification by the Partnership. The Partnership agrees to indemnify each Purchaser and its
Representatives (collectively, “Purchaser Related Parties”) from, and hold each of them harmless against, any and all actions, suits, proceedings (including any investigations, litigation or inquiries), demands, and causes of
action, and, in connection therewith, and promptly upon demand, pay or reimburse each of them for all costs, losses, liabilities, damages, or expenses of any kind or nature whatsoever, including the reasonable fees and disbursements of counsel and
all other reasonable expenses incurred in connection with investigating, defending or preparing to defend any such matter that may be incurred by them or asserted against or involve any of them as a result of, arising out of, or in any way related
to the breach of any of the representations, warranties or covenants of the Partnership contained herein, provided that such claim for indemnification relating to a breach of the representations or warranties is made prior to the expiration of such
representations or warranties; and provided further, that no Purchaser Related Party shall be entitled to recover special, indirect, incidental, consequential (including lost profits or diminution in value) or punitive damages. Notwithstanding
anything to the contrary, indirect, incidental and consequential damages shall not be deemed to include diminution in value of the Purchased Units to the extent resulting from, arising out of or in any way related to the breach of any of the
representations, warranties or covenants of the Partnership contained herein, which is specifically included in damages covered by the Purchaser Related Parties’ indemnification. 

Section 6.2 Indemnification by Purchasers. Each Purchaser agrees, severally and not jointly, to indemnify the
Partnership, the General Partner and their respective Representatives (collectively, “Partnership Related Parties”) from, and hold each of them harmless against, any and all actions, suits, proceedings (including any investigations,
litigation or inquiries), demands, and causes of action, and, in connection therewith, and promptly upon demand, pay or reimburse each of them for all costs, losses, liabilities, damages, or expenses of any kind or nature whatsoever, including the
reasonable fees and disbursements of counsel and all other reasonable expenses incurred in connection with investigating, defending or preparing to defend any such matter that may be incurred by them or asserted against or involve any of them as a
result of, arising out of, or in any way related to the breach of any of the representations, warranties or covenants of such Purchaser contained herein, provided that such claim for indemnification relating to a breach of the representations and
warranties is made prior to the expiration of such representations and warranties; and provided further, that no Partnership Related Party shall be entitled to recover special, indirect, incidental, consequential (including lost profits or
diminution in value) or punitive damages. 

  
 21 

 Section 6.3 Indemnification Procedure. Promptly after any
Partnership Related Party or Purchaser Related Party (hereinafter, the “Indemnified Party”) has received notice of any indemnifiable claim hereunder, or the commencement of any action, suit or proceeding by a third person, which the
Indemnified Party believes in good faith is an indemnifiable claim under this Agreement, the Indemnified Party shall give the indemnitor hereunder (the “Indemnifying Party”) written notice of such claim or the commencement of such
action, suit or proceeding, but failure to so notify the Indemnifying Party will not relieve the Indemnifying Party from any liability it may have to such Indemnified Party hereunder except to the extent that the Indemnifying Party is materially
prejudiced by such failure. Such notice shall state the nature and the basis of such claim to the extent then known. The Indemnifying Party shall have the right to defend and settle, at its own expense and by its own counsel who shall be reasonably
acceptable to the Indemnified Party, any such matter as long as the Indemnifying Party pursues the same diligently and in good faith. If the Indemnifying Party undertakes to defend or settle any such action or claim, it shall promptly notify the
Indemnified Party of its intention to do so, and the Indemnified Party shall cooperate with the Indemnifying Party and its counsel in all commercially reasonable respects in the defense thereof and the settlement thereof. Such cooperation shall
include, but shall not be limited to, furnishing the Indemnifying Party with any books, records and other information reasonably requested by the Indemnifying Party and in the Indemnified Party’s possession or control. Such cooperation of the
Indemnified Party shall be at the cost of the Indemnifying Party. After the Indemnifying Party has notified the Indemnified Party of its intention to undertake to defend or settle any such asserted liability, and for so long as the Indemnifying
Party diligently pursues such defense, the Indemnifying Party shall not be liable for any additional legal expenses incurred by the Indemnified Party in connection with any defense or settlement of such asserted liability; provided, however, that
the Indemnified Party shall be entitled (i) at its expense, to participate in the defense of such asserted liability and the negotiations of the settlement thereof and (ii) if (A) the Indemnifying Party has failed to assume the
defense or employ counsel reasonably acceptable to the Indemnified Party or (B) if the defendants in any such action include both the Indemnified Party and the Indemnifying Party and counsel to the Indemnified Party shall have concluded that
there may be reasonable defenses available to the Indemnified Party that are different from or in addition to those available to the Indemnifying Party or if the interests of the Indemnified Party reasonably may be deemed to conflict with the
interests of the Indemnifying Party, then the Indemnified Party shall have the right to select a separate counsel and to assume such legal defense and otherwise to participate in the defense of such action, with the expenses and fees of such
separate counsel and other expenses related to such participation to be reimbursed by the Indemnifying Party as incurred. Notwithstanding any other provision of this Agreement, the Indemnifying Party shall not settle any indemnified claim without
the consent of the Indemnified Party, unless the settlement thereof imposes no liability or obligation on, includes a complete release from liability of, and does not include any admission of wrongdoing or malfeasance by, the Indemnified Party. 

  
 22 

 ARTICLE VII 

MISCELLANEOUS 

Section 7.1 Interpretation and Survival of Provisions. Article, Section, Schedule, and Exhibit references are to
this Agreement, unless otherwise specified. All references to instruments, documents, contracts, and agreements are references to such instruments, documents, contracts, and agreements as the same may be amended, supplemented, and otherwise modified
from time to time, unless otherwise specified. The word “including” shall mean “including but not limited to.” Whenever any party has an obligation under the Operative Documents, the expense of complying with that obligation
shall be an expense of such party unless otherwise specified. Whenever any determination, consent, or approval is to be made or given by any Purchaser, such action shall be in such Purchaser’s sole discretion unless otherwise specified in the
Operative Documents. If any provision in the Operative Documents is held to be illegal, invalid, not binding, or unenforceable, such provision shall be fully severable and the Operative Documents shall be construed and enforced as if such illegal,
invalid, not binding, or unenforceable provision had never comprised a part of the Operative Documents, and the remaining provisions shall remain in full force and effect. The Operative Documents have been reviewed and negotiated by sophisticated
parties with access to legal counsel and shall not be construed against the drafter. 
 Section 7.2 Survival of
Provisions. The representations and warranties set forth in Sections 3.1, 3.2, 3.6, 3.9, 3.10 (first sentence), 3.17, 4.4, 4.5, 4.7, 4.8, 4.9, and 4.13 hereunder shall survive the execution and delivery of this Agreement
indefinitely, and the other representations and warranties set forth herein shall survive for a period of twelve (12) months following the Closing Date regardless of any investigation made by or on behalf of the Partnership or any Purchaser.
The covenants and agreements made in this Agreement, including the covenants and agreements set forth in this Article VII, or any other Operative Document shall survive the Closing of the transactions described herein and remain operative and in
full force and effect regardless of acceptance of any of the Purchased Units and payment therefor and repayment, conversion, exercise or repurchase thereof. All indemnification obligations of the Partnership and the Purchasers pursuant to this
Agreement and the provisions of Article VI shall remain operative and in full force and effect unless such obligations are expressly terminated in a writing by the parties, regardless of any purported general termination of this Agreement. 

Section 7.3 No Waiver; Modifications in Writing. 

(a) Delay. No failure or delay on the part of any party in exercising any right, power, or remedy hereunder shall
operate as a waiver thereof, nor shall any single or partial exercise of any such right, power, or remedy preclude any other or further exercise thereof or the exercise of any other right, power, or remedy. The remedies provided for herein are
cumulative and are not exclusive of any remedies that may be available to a party at law or in equity or otherwise. 
 (b)
Specific Waiver. Except as otherwise provided herein, no amendment, waiver, consent, modification, or termination of any provision of this Agreement or any other Operative Document shall be effective unless signed by each of the parties
thereto. Any amendment, supplement or modification of or to any provision of this Agreement or any other Operative Document, any waiver of any provision of this Agreement or any other Operative Document, and any consent to any departure by the
Partnership from the terms of any provision of this Agreement or any other Operative Document shall be effective only in the specific instance and for the specific purpose for which made or given. Except where notice is specifically required by this
Agreement, no notice to or demand on the Partnership in any case shall entitle the Partnership to any other or further notice or demand in similar or other circumstances. 

  
 23 

 Section 7.4 Binding Effect; Assignment. 

(a) Binding Effect. This Agreement shall be binding upon the Partnership, the Purchasers, and their respective
successors and permitted assigns. Except as expressly provided in this Agreement, this Agreement shall not be construed so as to confer any right or benefit upon any Person other than the parties to this Agreement and their respective successors and
permitted assigns. 
 (b) Assignment of Rights. All or any portion of the rights and obligations of any Purchaser
under this Agreement may be transferred by such Purchaser to any Affiliate of such Purchaser without the consent of the Partnership. No portion of the rights and obligations of any Purchaser under this Agreement may be transferred by such Purchaser
to a non-Affiliate without the prior written consent of the Partnership (which consent shall not be unreasonably withheld by the Partnership). As a condition to any assignment hereunder, the assignee shall agree in writing to be bound by the
provisions of this Agreement. The Partnership may not transfer any of its rights or obligations under this Agreement to any Person, except as expressly set forth herein. 

Section 7.5 Communications. All notices and demands provided for hereunder shall be in writing and shall be given
by registered or certified mail, return receipt requested, telecopy, air courier guaranteeing overnight delivery or personal delivery to the following addresses: 
  

	 	(a)	 If to any Purchaser: 

To its respective address listed on Schedule B hereof 

 

	 	(b)	 If to the Partnership: 

Teekay Offshore Partners L.P. 

4th Floor, Belvedere Building 

69 Pitts Bay Road 

Hamilton HM 08, Bermuda 

Attention: Corporate Secretary 

Facsimile: (441) 292-3931 

with a copy to: 

Perkins Coie LLP 

1120 N.W. Couch Street, 10th Floor 

Portland, Oregon 97209-4128 

Attention: David Matheson 

Facsimile: (503) 346-2008 

  
 24 

 or to such other address as the Partnership or such Purchaser may designate in writing. All
notices and communications shall be deemed to have been duly given: at the time delivered by hand, if personally delivered; upon actual receipt if sent by certified mail, return receipt requested, or regular mail, if mailed; when receipt
acknowledged, if sent via facsimile; and upon actual receipt when delivered to an air courier guaranteeing overnight delivery. 

Section 7.6 Removal of Legend. In connection with a sale of the Purchased Units by a Purchaser in reliance on Rule
144, the applicable Purchaser or its broker shall deliver to the Partnership a broker representation letter providing to the Partnership any information the Partnership deems necessary to determine that the sale of the Purchased Units is made in
compliance with Rule 144, including, as may be appropriate, a certification that the Purchaser is not an Affiliate of the Partnership and regarding the length of time the Purchased Units have been held. After a registration statement under the
Securities Act permitting the public resale of the Purchased Units has become effective or any Purchaser or its permitted assigns have held the Purchased Units for six months, if the certificate for such Purchased Units or the book-entry account of
such Purchased Units still bears the notation of the restrictive legend referred to in Section 4.9, the Partnership agrees, upon request of the Purchaser or permitted assignee, to take all steps reasonably necessary to promptly effect the
removal of the legend from the Purchased Units, and the Partnership shall bear all costs associated therewith, regardless of whether the request is made in connection with a sale or otherwise, so long as such Purchaser or its permitted assigns
provide to the Partnership any information the Partnership deems necessary to determine that the legend is no longer required under the Securities Act or applicable state laws, including (if there is no such registration statement) a certification
that the holder is not an Affiliate of the Partnership (and a covenant to inform the Partnership if it should thereafter become an Affiliate and to consent to exchange its certificates for certificates bearing an appropriate restrictive legend) and
regarding the length of time the Purchased Units have been held. Assuming a registration statement is effective or the Purchased Units have been held for greater than six months, whether held in certificated form or in book entry with the transfer
agent, the Partnership agrees that upon request, it shall cooperate with the Purchaser to have the Purchased Units moved to such Purchaser’s DTC custodial or brokerage account according to the instructions provided by such Purchaser. 

Section 7.7 Entire Agreement. This Agreement and the other Operative Documents and the other agreements and
documents referred to herein are intended by the parties as a final expression of their agreement and intended to be a complete and exclusive statement of the agreement and understanding of the parties hereto and thereto in respect of the subject
matter contained herein and therein. There are no restrictions, promises, warranties or undertakings, other than those set forth or referred to herein or the other Operative Documents with respect to the rights granted by the Partnership or any of
its Affiliates or any Purchaser or any of its Affiliates set forth herein or therein. This Agreement, the other Operative Documents and the other agreements and documents referred to herein or therein supersede all prior agreements and
understandings between the parties with respect to such subject matter. 

  
 25 

 Section 7.8 Governing Law. This Agreement will be construed in
accordance with and governed by the laws of the State of New York without regard to principles of conflicts laws thereof that would apply the laws of any other jurisdiction. 

Section 7.9 Execution in Counterparts. This Agreement may be executed in any number of counterparts and by
different parties hereto in separate counterparts, including facsimile or .pdf format counterparts, each of which counterparts, when so executed and delivered, shall be deemed to be an original and all of which counterparts, taken together, shall
constitute but one and the same Agreement. 
 Section 7.10 Termination. 

(a) Notwithstanding anything herein to the contrary, this Agreement may be terminated at any time at or prior to the Closing by
(i) with respect to any particular Purchaser, the written notice by such Purchaser to the Partnership upon a breach in any material respect by the Partnership of any covenant or agreement set forth in this Agreement or (ii) with respect to
any particular Purchaser, written notice by the Partnership to such Purchaser upon a breach in any material respect by such Purchaser of any covenant or agreement set forth in this Agreement. For the avoidance of doubt, the termination of this
Agreement with respect to any particular Purchaser shall not affect the Agreement with respect to any other Purchaser. 

(b) Notwithstanding anything herein to the contrary, this Agreement shall automatically terminate (i) at any time at or
prior to the Closing if a statute, rule, order, decree or regulation shall have been enacted or promulgated, or if any action shall have been taken by any Governmental Authority of competent jurisdiction that permanently restrains, permanently
precludes, permanently enjoins or otherwise permanently prohibits the consummation of the transactions contemplated by this Agreement or makes the transactions contemplated by this Agreement illegal or (ii) if the Closing shall not have
occurred by July 15, 2016. 
 (c) In the event of the termination of this Agreement as provided in this
Section 7.10, (1) this Agreement shall forthwith become null and void as to the applicable Parties, and (2) there shall be no liability on the part of such Parties hereto, except as set forth in Sections 5.3 and
Article VI of this Agreement; provided, however, that nothing herein shall relieve any Party from any liability or obligation with respect to any willful breach of this Agreement. 

Section 7.11 Recapitalization, Exchanges, Etc. Affecting the Common Units. The provisions of this Agreement shall
apply to the full extent set forth herein with respect to any and all equity interests of the Partnership or any successor or assign of the Partnership (whether by merger, consolidation, sale of assets or otherwise) which may be issued in respect
of, in exchange for or in substitution of, the Common Units, and shall be appropriately adjusted for combinations, recapitalizations and the like occurring after the date of this Agreement and prior to the Closing. 

Section 7.12 Disclosure. Each Purchaser agrees not to disclose information about this Agreement, the Registration
Rights Agreement and the transactions contemplated hereby until and to the extent the Partnership publicly discloses such information. The Partnership shall disclose on Commission Form 6-K, within four Business Days of the date of this Agreement,
the transactions contemplated by this Agreement and the Registration Rights Agreement. 
 [Signature pages follow] 

  
 26 

 IN WITNESS WHEREOF, the parties hereto execute this Agreement, effective as of
the date first above written. 
  

			
	TEEKAY OFFSHORE PARTNERS L.P.
		
	By:	 	TEEKAY OFFSHORE GP L.L.C.
		 	(its General Partner)
		
	By:	 	/s/ Peter Evensen
		 	Name: Peter Evensen
		 	Title: Chief Executive Officer and Chief Financial Officer

 
			
	PURCHASER:
	
	MTP ENERGY FUND LTD
		
	By:	 	MTP Energy Management LLC, its Investment Advisor
	By:	 	Magnetar Financial LLC, its Sole Member
		
	By:	 	/s/ Michael Turro
		 	Name: Michael Turro
		 	Title: Chief Compliance Officer

 
			
	PURCHASERS:
	
	TRIANGLE PEAK PARTNERS II, LP
		
	By:	 	Triangle Peak Partners II General Partner, LLC, its General Partner
		
	By:	 	/s/ Michael C. Morgan
		 	Name: Michael C. Morgan
		 	Title: Manager
	
	TPP II ANNEX FUND, LP
		
	By:	 	Triangle Peak Partners II General Partner, LLC, its General Partner
		
	By:	 	/s/ Michael C. Morgan
		 	Name: Michael C. Morgan
		 	Title: Manager

 
			
	PURCHASER:
	
	Nuveen Energy MLP Total Return Fund
		
	By:	 	/s/ Quinn T. Kiley
		 	Name: Quinn T. Kiley
		 	Title: Portfolio Manager

 
			
	PURCHASER:
	
	Advisory Research MLP & Energy Infrastructure Fund
		
	By:	 	/s/ Quinn T. Kiley
		 	Name: Quinn T. Kiley
		 	Title: Portfolio Manager

 
			
	PURCHASER:
	
	Fiduciary/Claymore MLP Opportunity Fund
		
	By:	 	/s/ Quinn T. Kiley
		 	Name: Quinn T. Kiley
		 	Title: Portfolio Manager

 
			
	PURCHASER:
	
	Nuveen All Cap Energy MLP Opportunities Fund
		
	By:	 	/s/ Quinn T. Kiley
		 	Name: Quinn T. Kiley
		 	Title: Portfolio Manager

 
			
	PURCHASER:
	
	Eagle Global SPV, LLC
		
	By:	 	/s/ David Chiaro
		 	Name: David Chiaro
		 	Title: Partner

 
			
	PURCHASER:
	
	Eagle Income Appreciation Partners, LP
		
	By:	 	/s/ David Chiaro
		 	Name: David Chiaro
		 	Title: Partner

 
			
	PURCHASER:
	
	Eagle Income Appreciation II, LP
		
	By:	 	/s/ David Chiaro
		 	Name: David Chiaro
		 	Title: Partner

 
			
	PURCHASER:
	
	Salient MLP Fund L.P.
	
	By: Salient Capital Advisors, LLC
	Its Investment Manager
		
	By:	 	/s/ Gregory A. Reid
		 	Name: Gregory A. Reid
		 	Title: Managing Director

 
			
	PURCHASER:
	
	Salient MLP TE Fund L.P.
	
	By: Salient Capital Advisors, LLC
	Its Investment Manager
		
	By:	 	/s/ Gregory A. Reid
		 	Name: Gregory A. Reid
		 	Title: Managing Director

 
			
	PURCHASER:
	
	Salient Midstream & MLP Fund
	
	By: Salient Capital Advisors, LLC
	Its Investment Manager
		
	By:	 	/s/ Gregory A. Reid
		 	Name: Gregory A. Reid
		 	Title: Managing Director

 
			
	PURCHASER:
	
	Salient MLP & Energy Infrastructure Fund
	
	By: Salient Capital Advisors, LLC
	Its Investment Manager
		
	By:	 	/s/ Gregory A. Reid
		 	Name: Gregory A. Reid
		 	Title: Managing Director

 
			
	PURCHASER:
	
	HITE Hedge GP LP
		
	By:	 	/s/ James Jampel
		 	Name: James Jampel
		 	Title: President

 
			
	PURCHASER:
	
	 HITE Hedge LP

		
	 By:
	 	 /s/ James Jampel

		 	 Name: James Jampel

		 	 Title: President

 
			
	PURCHASER:
	
	 HITE Hedge Offshore, Ltd

		
	 By:
	 	 /s/ James Jampel

		 	 Name: James Jampel

		 	 Title: President

 
			
	PURCHASER:
	
	 HITE MLP LP

		
	 By:
	 	 /s/ James Jampel

		 	 Name: James Jampel

		 	 Title: President

 
			
	PURCHASER:
	
	 HITE MLP Caymans, Ltd.

		
	 By:
	 	 /s/ James Jampel

		 	 Name: James Jampel

		 	 Title: President

 
			
	PURCHASER:
	
	 HITE MLP Advantage LP

		
	 By:
	 	 /s/ James Jampel

		 	 Name: James Jampel

		 	 Title: President

 
			
	PURCHASER:
	
	 Brookfield Investment Management Inc.

		
	 By:
	 	 /s/ Seth Gelman

		 	 Name: Seth Gelman

		 	 Title: Chief Compliance Officer

 
			
	PURCHASER:
	
	 LUMINUS ENERGY PARTNERS MASTER FUND, LTD.

	
	 By: Luminus Management, LLC

	 Its: Investment Manager

		
	 By:
	 	 /s/ Jeffrey Wade

		 	 Name: Jeffrey Wade

		 	 Title: General Counsel

 Schedule A – List of Purchasers and Commitment Amounts 

 

									
	 Purchaser
	  	Common
Units	 	  	Purchase Price*	 
	 MTP Energy Fund Ltd
	  	 	5,142,858	  	  	 	23,400,003.90	  
	 Triangle Peak Partners II, LP
	  	 	65,934	  	  	 	299,999.70	  
	 TPP II Annex Fund, LP
	  	 	285,714	  	  	 	1,299,998.70	  
	 Nuveen Energy MLP Total Return Fund
	  	 	1,969,120	  	  	$	8,959,496.00	  
	 Advisory Research MLP & Energy Infrastructure Fund
	  	 	589,250	  	  	$	2,681,087.50	  
	 Fiduciary / Claymore MLP Opportunity Fund
	  	 	2,151,180	  	  	$	9,787,869.00	  
	 Nuveen All Cap Energy MLP Opportunities Fund
	  	 	125,613	  	  	$	571,539.15	  
	 Eagle Global SPV, LLC
	  	 	274,750	  	  	$	1,250,113	  
	 Eagle Income Appreciation Partners, LP
	  	 	1,279,144	  	  	$	5,820,105	  
	 Eagle Income Appreciation II, LP
	  	 	2,292,260	  	  	$	10,429,783	  
	 Salient MLP Fund L.P.
	  	 	1,002,582	  	  	$	4,561,748.10	  
	 Salient MLP TE Fund L.P
	  	 	173,154	  	  	$	787,850.70	  
	 Salient Midstream & MLP Fund
	  	 	739,218	  	  	$	3,363,441.90	  
	 Salient MLP & Energy Infrastructure Fund
	  	 	1,931,200	  	  	$	8,786,960.00	  
	 HITE Hedge QP LP
	  	 	501,099	  	  	$	2,280,000.45	  
	 HITE Hedge LP
	  	 	632,968	  	  	$	2,880,004.40	  
	 HITE Hedge Offshore, Ltd
	  	 	501,099	  	  	$	2,280,000.45	  
	 HITE MLP LP
	  	 	474,725	  	  	$	2,159,998.75	  
	 HITE MLP Caymans, Ltd.
	  	 	263,736	  	  	$	1,199,998.80	  
	 HITE MLP Advantage LP
	  	 	263,736	  	  	$	1,199,998.80	  
	 Brookfield Global Listed Infrastructure Partners LP
	  	 	659,341	  	  	$	3,000,001.55	  
	 Luminus Energy Partners Master Fund, Ltd.
	  	 	659,341	  	  	$	3,000,001.55	  
		  	  
	  
	 	  	  
	  
	 
	 TOTAL:
	  	 	21,978,022	  	  	$	100,000,000.40	  
		  	  
	  
	 	  	  
	  
	 

  

	*	 The Purchase Price for each Purchaser is equal to the product of (i) the number of Common Units set forth
opposite such Purchaser’s name under the column titled “Common Units” above, multiplied by (ii) $4.55. 

 Schedule 3.13 – Litigation 

See Item 1 – Financial Statements: Note 10(h) and (i)– Commitments and Contingencies, in the Partnership’s Form 6-K
for the quarter ended March 31, 2016. 

 Exhibit A – Form of Registration Rights Agreement 

 Exhibit B – Form of Opinion of Perkins Coie LLP 

Capitalized terms used but not defined herein have the meanings assigned to such terms in the Common Unit Purchase Agreement (the
“Purchase Agreement”). The Partnership shall furnish to the Purchasers at the Closing an opinion of Perkins Coie LLP, counsel for the Partnership, addressed to the Purchasers and dated the Closing Date in form reasonably
satisfactory to the Purchasers, stating that: 
 (i) To our knowledge, except as contemplated by the Series C
Transaction, the Series D Offering and as described in the Partnership SEC Documents filed prior to the date of the Purchase Agreement, there are no outstanding options, warrants, or agreements for the purchase or acquisition from the Partnership of
Partnership securities or ownership interests in the Partnership, or rights to convert any obligations into or exchange any securities for Partnership securities or ownership interests in the Partnership. 

(ii) All consents, approvals, authorizations or other orders of, or registrations or filings on the part of the Partnership
with, any United States federal or New York governmental or regulatory authority required for the Partnership’s execution and delivery of the Operative Documents and the consummation of the Transactions, including the offering, issuance and
sale of the Purchased Units, have been made or obtained, other than (a) those required by the Commission in connection with the Partnership’s obligations under the Registration Rights Agreement and (b) those that have been obtained or
as may be required under state securities or “Blue Sky” laws, as to which we do not express any opinion. 
 (iii)
To our knowledge, there are no contracts, agreements or understandings between any of the Teekay Entities and any person granting such person the right to require any of the Teekay Entities to file a registration statement under the Act with respect
to any securities of the Partnership owned or to be owned by such person or to require any of the Teekay Entities to include such securities in any securities being registered pursuant to any other registration statement filed by any Teekay Entity
under the Act, except for the Registration Rights Agreement, the Series D Registration Rights Agreement, the Existing Registration Rights Agreements, and any such rights held by the General Partner or an Affiliate (as defined in the Partnership
Agreement) of the General Partner pursuant to the Partnership Agreement. 
 (iv) The Partnership’s offering, issuance
and sale of the Purchased Units and the Partnership’s execution and delivery of the Operative Documents and consummation of the Transactions do not (i) breach or result in a default under (or constitute an event which, with notice or lapse
of time or both, would constitute such a default) any Material Agreement, or (ii) violate statutory U.S. federal laws or the laws of the State of New York that counsel exercising customary professional judgment would in our experience
reasonably recognize as typically applicable to agreements similar to the Operative Documents and the Transactions. “Material Agreement” means any indenture, contract, mortgage, deed of trust, note agreement, loan agreement, lease or other
agreement or instrument filed by the Partnership as an exhibit to the Partnership’s Annual Report on Form 20-F for the year ended December 31, 2015, filed with the Commission on April 18, 2016. 

 (v) Assuming the Operative Documents have been duly authorized, executed and
delivered by the Partnership, each of the Operative Documents will constitute a valid and legally binding agreement of the Partnership, enforceable against the Partnership in accordance with its terms. 

(vi) Based in part upon the Partnership’s and the Purchasers’ representations and warranties in, and on the facts and
circumstances contemplated by, the Purchase Agreement, the offer, issuance and sale of the Purchased Units by the Partnership to the Purchasers pursuant to the terms of the Purchase Agreement do not require registration under Section 5 of the
Securities Act. (We do not comment or opine as to any subsequent sale of the Purchased Units). 
 (vii) The Partnership is
not, and immediately after giving effect to the use of proceeds from the sale of the Purchased Units pursuant to the Purchase Agreement will not be, required to register as an “investment company” under the Investment Company Act of 1940,
as amended. 

 Exhibit C – Form of Opinion of Watson Farley & Williams LLP 

Capitalized terms used but not defined herein have the meanings assigned to such terms in the Common Unit Purchase
Agreement (the “Purchase Agreement”). The Partnership shall furnish to the Purchasers at the Closing an opinion of Watson, Farley & Williams LLP, special counsel relating to Marshall Islands law for the Partnership,
addressed to the Purchasers and dated the Closing Date in form reasonably satisfactory to the Purchasers, stating that: 

(i) Each of the Partnership and the Operating Company has been duly formed and is validly existing in good standing as a
limited partnership under the law of the Republic of the Marshall Islands, and has the limited partnership power and authority to own or lease its properties and to conduct its business, in each case in all material respects as described in the
Partnership SEC Documents. 
 (ii) Each of the General Partner and the OLP GP has been duly formed and is validly existing in
good standing as a limited liability company under the law of the Republic of the Marshall Islands, and each has the limited liability company power and authority to own or lease its properties and to conduct its business, in each case in all
material respects as described in the Partnership SEC Documents. 
 (iii) Each of the entities listed in
Schedule A to such opinion (the “Marshall Islands Significant Subsidiaries”) is validly existing in good standing as a limited liability company or corporation, as applicable, under Marshall Islands Law, and each has the
limited liability company or corporate power, as applicable, and authority to own or lease its properties and to conduct its business, in each case in all material respects as described in the Partnership SEC Documents. 

(iv) The Purchased Units and the limited partner interests represented thereby have been duly authorized in accordance with the
Partnership Agreement and, when issued and delivered to the Purchasers against payment therefor in accordance with the terms of the Agreement, will be validly issued, fully paid (to the extent required under the Partnership Agreement) and
nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and except as may otherwise be provided in the Partnership Agreement). 

(v) Except as described in the Partnership SEC Documents and except as contained in Articles V, VII, XI, XV and XVI of the
Partnership Agreement, the Partnership Agreement does not contain any preemptive rights or other rights to subscribe for or to purchase any limited partner interests in the Partnership. 

 (vi) The execution, delivery and performance of the Agreement and the
consummation of the transactions contemplated thereby, including the offering, issuance and sale by the Partnership of the Purchased Units in accordance with and upon the terms and conditions set forth in the Agreement, do not (A) conflict with
or constitute a violation of the organizational documents of the Partnership, the General Partner, the Operating Company, the OLP GP or the Marshall Islands Significant Subsidiaries, (B) conflict with or constitute a breach or violation of, or
a default under (or an event which, with notice or lapse of time or both, would constitute such a default), the agreements or instruments governed by Marshall Islands Law and listed on a schedule to such opinion, (C) violate Marshall Islands
Law, or (D) violate any judgment, order or decree of which we are aware of any court, regulatory body, administrative agency, governmental body, arbitrator or other authority situated in the Republic of The Marshall Islands directed to any of
the Partnership, the General Partner, the Operating Company, the OLP GP or the Marshall Islands Significant Subsidiaries in a proceeding before such court, regulatory body, administrative agency, governmental body, arbitrator or other authority in
the Republic of the Marshall Islands to which any of them is a party. 
 (vii) No permit, consent, approval, authorization,
order, registration, filing or qualification of or with any court, governmental agency or body of the Republic of The Marshall Islands having jurisdiction over the Partnership, the General Partner, the Operating Company, the OLP GP or the Marshall
Islands Significant Subsidiaries or any of their respective properties is required in connection with the execution and delivery of the Agreement by the General Partner in its capacity as the general partner of the Partnership, the performance of
the transactions contemplated hereby by the Partnership Entities or the performance by the Partnership of its obligations hereunder, including the offering, issuance and sale by the Partnership of the Purchased Units in accordance with and upon the
terms and conditions set forth in the Agreement. 
 (viii) The choice of New York law to govern the Agreement constitutes a
valid choice of law under Marshall Islands Law. 
 (ix) The Agreement has been duly authorized and validly executed by the
General Partner in its capacity as the general partner of the Partnership.EX-10.2

 Exhibit 10.2 
  

 
  

SERIES D PREFERRED UNIT AND WARRANT 

PURCHASE AGREEMENT 
 by
and among 
 TEEKAY OFFSHORE PARTNERS L.P. 

and 
 THE PURCHASERS
NAMED ON SCHEDULE A HERETO 
  
  

 

							
	 ARTICLE I DEFINITIONS
	  	 	1	  
			
	 Section 1.1
	 	 Definitions
	  	 	1	  
		
	 ARTICLE II AGREEMENT TO SELL AND PURCHASE
	  	 	6	  
			
	 Section 2.1
	 	 Sale and Purchase
	  	 	6	  
	 Section 2.2
	 	 Closing
	  	 	6	  
	 Section 2.3
	 	 Allocation of Purchased Unit Price
	  	 	7	  
	 Section 2.4
	 	 Mutual Conditions
	  	 	7	  
	 Section 2.5
	 	 Each Purchaser’s Conditions
	  	 	7	  
	 Section 2.6
	 	 The Partnership’s Conditions
	  	 	8	  
	 Section 2.7
	 	 Partnership Deliveries
	  	 	9	  
	 Section 2.8
	 	 Purchaser Deliveries
	  	 	11	  
	 Section 2.9
	 	 Independent Nature of Purchasers’ Obligations and Rights
	  	 	11	  
		
	 ARTICLE III REPRESENTATIONS AND WARRANTIES OF THE PARTNERSHIP
	  	 	11	  
			
	 Section 3.1
	 	 Existence
	  	 	11	  
	 Section 3.2
	 	 Capitalization and Valid Issuance of Purchased Units
	  	 	12	  
	 Section 3.3
	 	 Subsidiaries
	  	 	14	  
	 Section 3.4
	 	 No Registration Required
	  	 	15	  
	 Section 3.5
	 	 No Conflict
	  	 	15	  
	 Section 3.6
	 	 No Default
	  	 	15	  
	 Section 3.7
	 	 Authority; Enforceability
	  	 	16	  
	 Section 3.8
	 	 Approvals
	  	 	16	  
	 Section 3.9
	 	 Compliance with Laws
	  	 	16	  
	 Section 3.10
	 	 Periodic Reports
	  	 	17	  
	 Section 3.11
	 	 Litigation
	  	 	17	  
	 Section 3.12
	 	 Insurance
	  	 	17	  
	 Section 3.13
	 	 Books and Records; Sarbanes Oxley Compliance
	  	 	17	  
	 Section 3.14
	 	 No Material Adverse Changes
	  	 	18	  
	 Section 3.15
	 	 Certain Fees
	  	 	18	  
	 Section 3.16
	 	 Investment Company Status
	  	 	18	  
	 Section 3.17
	 	 Passive Foreign Investment Company
	  	 	18	  
	 Section 3.18
	 	 Tax Status
	  	 	19	  
	 Section 3.19
	 	 Title to Property
	  	 	19	  
	 Section 3.20
	 	 No Side Agreements
	  	 	19	  
	 Section 3.21
	 	 Form F-3 Eligibility
	  	 	19	  
	 Section 3.22
	 	 Disclosure of Material Information
	  	 	19	  
	 Section 3.23
	 	 Foreign Corrupt Practices Act
	  	 	20	  

  
 i 

							
		
	 ARTICLE IV REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS
	  	 	20	  
			
	 Section 4.1
	 	 Existence
	  	 	20	  
	 Section 4.2
	 	 Authorization, Enforceability
	  	 	20	  
	 Section 4.3
	 	 No Breach
	  	 	20	  
	 Section 4.4
	 	 Certain Fees
	  	 	21	  
	 Section 4.5
	 	 Unregistered Securities
	  	 	21	  
	 Section 4.6
	 	 No Side Agreements
	  	 	22	  
	 Section 4.7
	 	 Short Selling
	  	 	22	  
	 Section 4.8
	 	 Purchaser Investigation; Partnership Projections
	  	 	22	  
		
	 ARTICLE V COVENANTS
	  	 	23	  
			
	 Section 5.1
	 	 Taking of Necessary Action
	  	 	23	  
	 Section 5.2
	 	 Other Actions
	  	 	23	  
	 Section 5.3
	 	 Short Sales; Hedging Transactions
	  	 	23	  
		
	 ARTICLE VI INDEMNIFICATION
	  	 	23	  
			
	 Section 6.1
	 	 Indemnification by the Partnership
	  	 	23	  
	 Section 6.2
	 	 Indemnification by Purchasers
	  	 	24	  
	 Section 6.3
	 	 Indemnification Procedure
	  	 	24	  
		
	 ARTICLE VII MISCELLANEOUS
	  	 	25	  
			
	 Section 7.1
	 	 Expenses
	  	 	25	  
	 Section 7.2
	 	 Interpretation
	  	 	25	  
	 Section 7.3
	 	 Survival of Provisions
	  	 	26	  
	 Section 7.4
	 	 No Waiver; Modifications in Writing
	  	 	26	  
	 Section 7.5
	 	 Binding Effect; Assignment
	  	 	27	  
	 Section 7.6
	 	 Disclosure
	  	 	27	  
	 Section 7.7
	 	 Communications
	  	 	27	  
	 Section 7.8
	 	 Entire Agreement
	  	 	28	  
	 Section 7.9
	 	 Removal of Legend
	  	 	29	  
	 Section 7.10
	 	 Governing Law
	  	 	29	  
	 Section 7.11
	 	 Execution in Counterparts
	  	 	29	  
	 Section 7.12
	 	 Termination
	  	 	29	  
	 Section 7.13
	 	 Recapitalization, Exchanges, Etc. Affecting the Common Units
	  	 	30	  

  

			
	 Schedule A —
	 	 List of Purchasers and Commitment Amounts

	 Schedule B —
	 	 Notice and Contact Information

	 Exhibit A —
	 	 Form of Warrant Agreement

	 Exhibit B —
	 	 Form of Opinion of Perkins Coie LLP

	 Exhibit C —
	 	 Form of Opinion of Watson Farley & Williams LLP

	 Exhibit D —
	 	 Form of General Partner Waiver

	 Exhibit E —
	 	 Form of Fifth Amended and Restated Agreement of Limited Partnership

	 Exhibit F —
	 	 Form of Registration Rights Agreement

  
 ii 

 SERIES D PREFERRED UNIT AND WARRANT PURCHASE AGREEMENT 

This SERIES D PREFERRED UNIT AND WARRANT PURCHASE AGREEMENT, dated June 22, 2016 (as further defined below, this
“Agreement”), is by and among TEEKAY OFFSHORE PARTNERS L.P., a Marshall Islands limited partnership (the “Partnership”), and the purchasers listed on Schedule A hereof (each a “Purchaser” and
collectively, the “Purchasers”). 
 WHEREAS, the Partnership desires to sell to the Purchasers, and the
Purchasers desire to purchase from the Partnership, certain Series D Preferred Units and Warrants (each as defined below), in accordance with the provisions of this Agreement. 

WHEREAS, in order to establish the Series D Preferred Units, the Partnership shall enter into the Fifth Amended and Restated
Agreement of Limited Partnership (as defined below). 
 WHEREAS, in connection with the issuance of the Series D Preferred
Units and Warrants pursuant to this Agreement, the Partnership and the Purchasers will enter into the Registration Rights Agreement (as defined below), pursuant to which the Partnership will provide the Purchasers with certain registration rights
with respect to the Underlying Units (as defined below). 
 WHEREAS, in connection with the Partnership’s
recapitalization plan, at or prior to the Closing, the Partnership intends to, (i) pursuant to the terms of a letter agreement between the Partnership and the holders of the Series C Preferred Units (as defined below) and related documentation
setting forth the terms of the Series C transaction (the “Series C Transaction”) exchange a portion of the outstanding Series C Preferred Units for Common Units and exchange the remaining Series C Preferred Units, on a one-for-one
basis, for a new series of preferred units of the Partnership designated as 8.60% Series C-1 Cumulative Convertible Perpetual Preferred Units (the “Series C-1 Preferred Units”), and (ii) issue Common Units (as defined
below) in a transaction exempt from the registration requirements of the Securities Act (as defined below), pursuant to the terms of a common unit purchase agreement entered into by and among the Partnership and the purchasers named on Schedule A
thereto (the “Common Unit Offering”). 
 NOW THEREFORE, in consideration of the mutual covenants and
agreements set forth herein and for good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, the Partnership and each of the Purchasers, severally and not jointly, hereby agree as follows: 

ARTICLE I 
 DEFINITIONS

 Section 1.1 Definitions. As used in this Agreement, and unless the context requires a different meaning,
the following terms have the meanings indicated: 
 “Affiliate” means, with respect to any Person, any
other Person that directly or indirectly through one or more intermediaries controls, is controlled by or is under common control with, the Person in question. As used herein, the term “control” means the possession, direct or indirect, of
the power to direct or cause the direction of the management and policies of a Person, whether through ownership of voting securities, by contract or otherwise. 

 “Agreement” has the meaning set forth in the introductory
paragraph, as amended, supplemented, continued or modified. 
 “Basic Documents” means, collectively, this
Agreement, the Registration Rights Agreement, the Warrant Agreement and, except as otherwise expressly set forth in this Agreement, the Fifth Amended and Restated Agreement of Limited Partnership. 

“Business Day” means a day other than (i) a Saturday or Sunday or (ii) any day on which banks
located in New York, New York, U.S.A. are authorized or obligated to close. 
 “Closing” has the meaning
specified in Section 2.2(a). 
 “Closing Date” has the meaning specified in
Section 2.2(a). 
 “Commission” means the United States Securities and Exchange Commission.

 “Common Unit Offering” has the meaning specified in the recitals hereto. 

“Common Units” means the Common Units representing limited partnership interests in the Partnership having
the rights and obligations specified in the Partnership Agreement. 
 “Conversion Units” means the Common
Units issuable upon conversion of the Series D Preferred Units. 
 “Exchange Act” means the Securities
Exchange Act of 1934, as amended from time to time, and the rules and regulations of the Commission promulgated thereunder. 

“FCPA” has the meaning specified in Section 3.23. 

“Fifth Amended and Restated Agreement of Limited Partnership” means that certain Fifth Amended and Restated
Agreement of Limited Partnership, to be executed on the Closing Date, in the form and substance attached hereto as Exhibit E. 

“General Partner” means Teekay Offshore GP L.L.C., a Marshall Islands limited liability company. 

“Governmental Authority” means, with respect to a particular Person, any country, state, county, city and
political subdivision in which such Person or such Person’s Property is located or that exercises valid jurisdiction over any such Person or such Person’s Property, and any court, agency, department, commission, board, bureau or
instrumentality of any of them and any monetary authority that exercises valid jurisdiction over any such Person or such Person’s Property. Unless otherwise specified, all references to Governmental Authority herein with respect to the
Partnership mean a Governmental Authority having jurisdiction over the Partnership, its Subsidiaries or any of their respective Properties. 

  
 2 

 “GP LLC Agreement” means the Amended and Restated Limited
Liability Company Agreement of the General Partner, dated December 19, 2006, as amended through the date hereof. 

“Indemnified Party” has the meaning specified in Section 6.3. 

“Indemnifying Party” has the meaning specified in Section 6.3. 

“Law” means any federal, state, local or foreign order, writ, injunction, judgment, settlement, award,
decree, statute, law, rule or regulation. 
 “Lien” means any mortgage, claim, encumbrance, pledge, lien
(statutory or otherwise), security agreement, conditional sale or trust receipt or a lease, consignment or bailment, preference or priority or other encumbrance upon or with respect to any property of any kind; provided, however, that any charter or
services contracts to which the Partnership’s vessels are subject shall not be deemed Liens. 

“Marshall Islands LLC Act” means the Marshall Islands Limited Liability Company Act of 1996, as amended. 

“Marshall Islands LP Act” means the Marshall Islands Limited Partnership Act. 

“Material Adverse Effect” means any change, event or effect that, individually or together with any other
changes, events or effects, has a material adverse effect on (i) the condition (financial or otherwise), business, assets or results of operations of the Partnership Entities, taken as a whole, (ii) the limited partners of the Partnership
resulting from any event which subjects them to any material liability, or (iii) the ability of the Partnership Entities to perform their obligations under the Basic Documents; provided, however, that a Material Adverse Effect shall not include
any material and adverse effect on the foregoing to the extent such material and adverse effect results from, arises out of, or relates to (w) the announcement of the transactions contemplated by this Agreement or the satisfaction of the
obligations set forth herein, (x) a general deterioration in the economy or changes in the general state of the industries in which the Partnership operates, except to the extent that the Partnership Entities, taken as a whole, is adversely
affected in a disproportionate manner as compared to other industry participants, (y) the outbreak or escalation of hostilities involving the United States, the declaration by the United States of a national emergency or war or the occurrence
of any other calamity or crisis, including acts of terrorism, or (z) any change in accounting requirements or principles imposed upon any Partnership Entity or their respective businesses or any change in applicable Law, or the interpretation
thereof. 
 “NYSE” means The New York Stock Exchange, Inc. 

“OLP GP” means Teekay Offshore Operating GP L.L.C., a Marshall Islands limited liability company. 

“Operating Company” means Teekay Offshore Operating L.P., a Marshall Islands limited partnership. 

  
 3 

 “Operative Agreements” has the meaning specified in
Section 3.1. 
 “Partnership” has the meaning set forth in the introductory paragraph. 

“Partnership Agreement” means the Fourth Amended and Restated Agreement of Limited Partnership of the
Partnership dated July 1, 2015, as amended to date. 
 “Partnership Entities” and each a
“Partnership Entity” means the General Partner, the Partnership and each of the Partnership’s Subsidiaries, other than those Subsidiaries which, individually, would not constitute a “significant subsidiary” as defined
in Regulation S-X. 
 “Partnership Related Parties” has the meaning specified in Section 6.2.

 “Partnership SEC Documents” has the meaning specified in Section 3.10. 

“Person” means an individual or a corporation, limited liability company, partnership, joint venture, trust,
unincorporated organization, association, government agency or political subdivision thereof or other form of entity. 

“Property” means any interest in any kind of property or asset, whether real, personal or mixed, or tangible
or intangible. 
 “Purchase Price” means, with respect to a particular Purchaser, the amount set forth
opposite such Purchaser’s name under the column titled “Purchase Price” set forth on Schedule A hereto. 

“Purchased Unit” means one Series D Preferred Unit, a Series A Warrant with respect to 1.125 Warrant Exercise
Units and a Series B Warrant with respect to 0.5625 Warrant Exercise Units. 
 “Purchased Unit Price” means
an amount per Purchased Unit of $25.00. 
 “Purchased Units” means, with respect to a particular Purchaser,
the number of Series D Preferred Units, the number of Warrant Exercise Units with respect to the Series A Warrant and the number of Warrant Exercise Units with respect to the Series B Warrant set forth opposite such Purchaser’s name under the
columns titled “Series D Preferred Units,” “Series A Warrant” and “Series B Warrant,” respectively, set forth on Schedule A attached hereto. 

“Purchaser” and “Purchasers” have the meanings set forth in the introductory paragraph. 

“Purchaser Related Parties” has the meaning specified in Section 6.1. 

“Registration Rights Agreement” means the Registration Rights Agreement, dated as of the Closing Date,
between the Partnership and the Purchasers, in the form and substance attached hereto as Exhibit F. 

  
 4 

 “Representatives” of any Person means the Affiliates, officers,
directors, managers, employees, agents, counsel, accountants, investment bankers and other representatives of such Person. 

“Securities” has the meaning specified in Section 4.5(a). 

“Securities Act” means the Securities Act of 1933, as amended from time to time, and the rules and
regulations of the Commission promulgated thereunder. 
 “Series A Preferred Units” has the meaning
specified in Section 3.2. 
 “Series A Warrant” means a Warrant, substantially in the form
attached to the Warrant Agreement as Exhibit A, to be issued to each Purchaser at the Closing. Each such Warrant, for the avoidance of doubt, may be transferred separately from the Series D Preferred Units and the Series B Warrant. 

“Series B Preferred Units” has the meaning specified in Section 3.2. 

“Series B Warrant” means a Warrant, substantially in the form attached to the Warrant Agreement as Exhibit
B, to be issued to each Purchaser at the Closing. Each such Warrant, for the avoidance of doubt, may be transferred separately from the Series D Preferred Units and the Series A Warrant. 

“Series C Preferred Units” has the meaning specified in Section 3.2. 

“Series C Transaction” has the meaning set forth in the recitals hereto. 

“Series C-1 Preferred Units” has the meaning set forth in the recitals hereto. 

“Series D Preferred Units” means the Partnership’s 10.5% Series D Cumulative Convertible Perpetual
Preferred Units. 
 “Short Sales” means, all “short sales” as defined in Rule 200 promulgated
under Regulation SHO under the Exchange Act, whether or not against the box, and forward sale contracts, options, puts, calls, short sales, “put equivalent positions” (as defined in Rule 16a-1(h) under the Exchange Act) and similar
arrangements, and sales and other transactions through non-U.S. broker dealers or foreign regulated brokers. 

“Subsidiary” means, as to any Person, any corporation or other entity of which: (i) such Person or a
Subsidiary of such Person is a general partner or manager; (ii) at least a majority of the outstanding equity interest having by the terms thereof ordinary voting power to elect a majority of the board of directors or similar governing body of
such corporation or other entity (irrespective of whether or not at the time any equity interest of any other class or classes of such corporation or other entity shall have or might have voting power by reason of the happening of any contingency)
is at the time directly or indirectly owned or controlled by such Person or one or more of its Subsidiaries; or (iii) any corporation or other entity as to which such Person consolidates for accounting purposes. 

  
 5 

 “Teekay Offshore Holdings” has the meaning specified in
Section 3.3(a). 
 “Underlying Units” means (i) the Conversion Units and (ii) the
Warrant Exercise Units. 
 “Warrant Agreement” means the agreement to be entered into at the Closing,
between the Partnership and Computershare Trust Company, N.A., substantially in the form attached hereto as Exhibit A. 

“Warrants” means the Series A Warrants and the Series B Warrants, collectively. 

“Warrant Exercise Units” means Common Units issuable upon exercise of the Warrants. 

ARTICLE II 
 AGREEMENT
TO SELL AND PURCHASE 
 Section 2.1 Sale and Purchase. 

(a) Subject to the terms and conditions hereof, (i) the Partnership hereby agrees to issue and sell to each Purchaser and
each Purchaser hereby agrees, severally and not jointly, to purchase from the Partnership, its respective Purchased Units, and (ii) each Purchaser agrees, severally and not jointly, to pay the Partnership the Purchased Unit Price for each
Purchased Unit as set forth in paragraph (b) below. The obligations of each Purchaser under this Agreement are independent of the obligations of each other Purchaser, and the failure or waiver of performance by any Purchaser does not excuse
performance by any other Purchaser or by the Partnership. 
 (b) The amount per Purchased Unit each Purchaser will pay to the
Partnership to purchase the Purchased Units hereunder shall be the Purchased Unit Price. 
 Section 2.2
Closing. 
 (a) Subject to the terms and conditions hereof, the consummation of the purchase and sale of Purchased
Units hereunder (the “Closing”) shall take place at the offices of Perkins Coie LLP, 1120 N.W. Couch Street, Tenth Floor, Portland, Oregon 97209-4128, or at such other location or on such other date as mutually agreed by the parties
and upon the satisfaction or waiver of the conditions set forth in Sections 2.4, 2.5 and 2.6 (the “Closing Date”). At the Closing, the Purchasers shall purchase Series D Preferred Units and Warrants as indicated
on Schedule A attached hereto. 
 (b) The parties agree that the Closing may occur via delivery of this Agreement and
other closing deliveries by facsimile, electronic mail, courier service or personal delivery. 

  
 6 

 Section 2.3 Allocation of Purchased Unit Price. Prior to the
Closing, the Partnership and the Purchasers shall use reasonable efforts to mutually agree upon the allocation of the Purchase Price among the Series D Preferred Units, the Series A Warrant (with respect to 1.125 Warrant Exercise Units) and the
Series B Warrant (with respect to 0.5625 Warrant Exercise Units) based upon their relative fair market values; provided, however, that if the Partnership and the Purchasers are unable to mutually agree upon such allocation, the allocation of the
Purchase Price shall be submitted to Ernst & Young LLP or such other firm mutually agreed by the Partnership and the Purchasers (the “Appraiser”) for determination. The Appraiser shall make such determination as promptly as
practicable after its appointment hereunder and may take into account all factors as such Appraiser deems appropriate in making such determination based upon the relative fair market values of the Series D Preferred Units, the Series A Warrant (with
respect to 1.125 Warrant Exercise Units) and the Series B Warrant (with respect to 0.5625 Warrant Exercise Units). The Appraiser shall have such access to the books, records and properties of the Partnership as it may reasonably request for the
purpose of making such a determination. 
 Section 2.4 Mutual Conditions. The respective obligations of each
party to consummate the purchase and issuance and sale of the Purchased Units shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions (any or all of which may be waived by a party on behalf of itself
in writing, in whole or in part, to the extent permitted by applicable Law): 
 (a) No Law shall have been enacted or
promulgated, and no action shall have been taken, by any Governmental Authority of competent jurisdiction that temporarily, preliminarily or permanently restrains, precludes, enjoins or otherwise prohibits the consummation of the transactions
contemplated by this Agreement or makes the transactions contemplated hereby illegal; 
 (b) There shall not be pending any
suit, action or proceeding by any Governmental Authority seeking to restrain, preclude, enjoin or prohibit the transactions contemplated by this Agreement; 

(c) The sum of (a) the aggregate Purchase Prices of the Purchasers paid for Purchased Units at the Closing and
(b) the aggregate purchase price of investors purchasing Common Units as part of the Common Unit Offering shall equal or exceed $200 million; and 

(d) The consent required to approve the Partnership’s proposed bond amendment has been obtained, and all conditions
precedent to the Partnership’s proposed bond amendment shall have been completed, on terms not materially different from those distributed to the Partnership’s bondholders on May 19, 2016 and without waiver of any conditions precedent
set forth therein other than with respect to the composition of the equity securities (preferred or common) to be sold by the Partnership. 

Section 2.5 Each Purchaser’s Conditions. The obligation of each Purchaser to consummate the purchase of its
Purchased Units shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions (any or all of which may be waived by a particular Purchaser on behalf of itself in writing with respect to its Purchased Units,
in whole or in part, to the extent permitted by applicable Law): 
 (a) The Partnership shall have performed and complied
with the covenants and agreements contained in this Agreement that are required to be performed and complied with by the Partnership on or prior to the Closing Date; 

  
 7 

 (b) The Underlying Units shall have been approved for listing on the NYSE,
subject to notice of issuance; 
 (c) (i) The representations and warranties of the Partnership contained in this Agreement
that are qualified by materiality or a Material Adverse Effect shall be true and correct when made and as of the Closing Date as if made on and as of the Closing Date (except that any such representations and warranties made as of a specific date
shall be required to be true and correct as of such date only) and (ii) all other representations and warranties of the Partnership contained in this Agreement shall be true and correct in all material respects when made and as of the Closing
Date as if made on and as of the Closing Date (except that any such representations and warranties made as of a specific date shall be required to be true and correct in all material respects as of such date only); 

(d) The Partnership shall have delivered, or caused to be delivered, to the Purchasers at the Closing, the Partnership’s
closing deliveries described in Section 2.7; 
 (e) No notice of delisting from the NYSE shall have been received
by the Partnership with respect to the Common Units; 
 (f) The Common Units shall not have been suspended by the Commission
or the NYSE from trading on the NYSE nor shall suspension by the Commission or the NYSE have been threatened in writing by the Commission or the NYSE; and 

(g) Since the date of this Agreement, no Material Adverse Effect shall have occurred. 

Section 2.6 The Partnership’s Conditions. The obligation of the Partnership to consummate the sale of
Purchased Units to a Purchaser shall be subject to the satisfaction on or prior to the Closing Date of each of the following conditions with respect to such Purchaser (any or all of which may be waived by the Partnership in writing, in whole or in
part, to the extent permitted by applicable Law): 
 (a) (i) The representations and warranties of such Purchaser contained
in this Agreement that are qualified by materiality shall be true and correct when made and as of the Closing Date (except that any such representations and warranties made as of a specific date shall be required to be true and correct as of such
date only) and (ii) all other representations and warranties of such Purchaser contained in this Agreement shall be true and correct in all material respects when made and as of the Closing Date (except that any such representations of such
Purchaser made as of a specific date shall be required to be true and correct in all material respects as of such date only); 

(b) Such Purchaser shall have delivered, or caused to be delivered, to the Partnership at the Closing such Purchaser’s
closing deliveries described in Section 2.8; 
 (c) A copy of the Warrant Agreement, duly executed by the
Transfer Agent; and 

  
 8 

 (d) By acceptance of the applicable Purchased Units, each Purchaser shall be
deemed to have represented to the Partnership that such Purchaser has performed and complied in all material respects with the covenants and agreements contained in this Agreement that are required to be performed and complied with by it on or prior
to the Closing Date; and the representations and warranties of such Purchaser contained in this Agreement that are qualified by materiality are true and correct as of the Closing Date (except that any such representations and warranties made as of a
specific date shall be required to be true and correct as of such date only) and all other representations and warranties of such Purchaser are true and correct in all material respects as of the Closing Date (except that any such representations
and warranties made as of a specific date shall be required to be true and correct in all material respects as of such date only). 

Section 2.7 Partnership Deliveries. At the Closing, subject to the terms and conditions hereof, the Partnership
will deliver, or cause to be delivered, to each Purchaser: 
 (a) Evidence of issuance of the Series D Preferred Units
purchased by the Purchasers at Closing credited to book-entry accounts maintained by the transfer agent, bearing a restrictive notation meeting the requirements of the Partnership Agreement, as amended by the Fifth Amended and Restated Agreement of
Limited Partnership, free and clear of any Liens, other than transfer restrictions under the Partnership Agreement, as amended by the Fifth Amended and Restated Agreement of Limited Partnership, or the Marshall Islands LP Act and applicable federal
and state securities laws; 
 (b) A Series A Warrant with respect to the number of Warrant Exercise Units under the Series A
Warrant column set forth opposite such Purchaser’s name on Schedule A in substantially the form attached as Exhibit A to the Warrant Agreement; 

(c) A Series B Warrant with respect to the number of Warrant Exercise Units under the Series B Warrant column set forth
opposite such Purchaser’s name on Schedule A in substantially the form attached as Exhibit B to the Warrant Agreement; 

(d) A “Supplemental Listing Application” approving the Underlying Units for listing by the NYSE, subject to notice of
issuance; 
 (e) A copy of the Fifth Amended and Restated Agreement of Limited Partnership, duly executed by the General
Partner, on behalf of itself and the limited partners of the Partnership, and Teekay Corporation. 
 (f) Copies of
(i) the Certificate of Limited Partnership of the Partnership and (ii) the Certificate of Formation of the General Partner, each certified by the Registrar of Corporations of the Republic of the Marshall Islands as of a recent date; 

(g) A certificate of the Registrar of Corporations of the Republic of the Marshall Islands, dated a recent date, to the effect
that each of the General Partner and the Partnership is in good standing; 

  
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 (h) A cross-receipt executed by the Partnership and delivered to such Purchaser
certifying that it has received the Purchase Price from such Purchaser as of the Closing Date; 
 (i) An opinion addressed to
the Purchasers from Perkins Coie LLP, legal counsel to the Partnership, dated as of the Closing Date, in the form and substance attached hereto as Exhibit B; 

(j) An opinion addressed to the Purchasers from Watson Farley & Williams LLP, special counsel to the Partnership,
relating to Marshall Islands law, dated as of the Closing Date, in the form and substance attached hereto as Exhibit C; 

(k) A certificate, dated the Closing Date and signed by the Chief Executive Officer and by the Chief Financial Officer, any
Vice President or Secretary of the General Partner, on behalf of the Partnership, in his or her capacities as such, stating that: 

(i) The Partnership has performed and complied with the covenants and agreements contained in this Agreement
that are required to be performed and complied with by the Partnership on or prior to the Closing Date; and 

(ii) The representations and warranties of the Partnership contained in this Agreement that are qualified by
materiality or Material Adverse Effect were true and correct when made and are true and correct as of the Closing Date and all other representations and warranties of the Partnership were true and correct in all material respects when made and are
true and correct in all material respects as of the Closing Date; in each case as though made at and as of the Closing Date (except that representations and warranties made as of a specific date shall be required to be true and correct or true and
correct in all material respects, as applicable, as of such date only); 
 (l) A certificate of the Secretary or Assistant
Secretary of the General Partner, on behalf of the Partnership, certifying as to (1) the Certificate of Limited Partnership of the Partnership and the Fifth Amended and Restated Agreement of Limited Partnership, (2) the Certificate of
Formation of the General Partner and the GP LLC Agreement, (3) board resolutions authorizing the execution and delivery of the Basic Documents and the consummation of the transactions contemplated thereby, including the issuance of the
Purchased Units and (4) the signatures of the officers executing this Agreement; 
 (m) A duly executed waiver of the
General Partner with respect to certain of its rights under the Partnership Agreement, in substantially the form attached hereto as Exhibit D; 

(n) The Registration Rights Agreement, duly executed by the Partnership and the General Partner; 

(o) A copy of the Warrant Agreement, duly executed by the General Partner, on behalf of the Partnership, and the Transfer
Agent; and 

  
 10 

 (p) Such other documents relating to the transactions contemplated by this
Agreement as the Purchasers or their counsel may reasonably request. 
 Section 2.8 Purchaser Deliveries. At
the Closing, subject to the terms and conditions hereof, each Purchaser will deliver, or cause to be delivered, to the Partnership: 

(a) Payment to the Partnership of the Purchase Price set forth opposite such Purchaser’s name under the column titled
“Purchase Price” on Schedule A hereto, by wire transfer of immediately available funds to an account designated by the Partnership in writing at least two Business Days prior to the Closing Date; 

(b) A cross-receipt executed by such Purchaser and delivered to the Partnership certifying that it has received its Purchased
Units, as of the Closing Date; and 
 (c) The Registration Rights Agreement, duly executed by such Purchaser. 

Section 2.9 Independent Nature of Purchasers’ Obligations and Rights. The obligations of each Purchaser
under this Agreement are several and not joint with the obligations of any other Purchaser, and no Purchaser shall be responsible in any way for the performance of the obligations of any other Purchaser under this Agreement. The failure or waiver of
performance under this Agreement of any Purchaser by the Partnership does not excuse performance by any other Purchaser and the waiver of performance of the Partnership by any Purchaser does not excuse performance by the Partnership with respect to
each other Purchaser. Nothing contained herein or in any other Basic Document, and no action taken by any Purchaser pursuant thereto, shall be deemed to constitute the Purchasers as a partnership, an association, a joint venture or any other kind of
group or entity, or create a presumption that the Purchasers are in any way acting in concert or as a group with respect to such obligations or the transactions contemplated by the Basic Documents. Each Purchaser shall be entitled to independently
protect and enforce its rights, including, the rights arising out of this Agreement or out of the other Basic Documents, and it shall not be necessary for any other Purchaser to be joined as an additional party in any proceeding for such purpose. It
is expressly understood and agreed that each provision contained in this Agreement is between the Partnership and a Purchaser, solely, and not between the Partnership and the Purchasers collectively and not between and among the Purchasers.
Notwithstanding anything to the contrary, for purposes of this Section the definition of “Basic Document” excludes the Fifth Amended and Restated Agreement of Limited Partnership. 

ARTICLE III 

REPRESENTATIONS AND WARRANTIES OF THE PARTNERSHIP 

The Partnership represents and warrants to each Purchaser as follows: 

Section 3.1 Existence. 

(a) Each of the Partnership Entities has been duly incorporated or formed, as the case may be, and is validly existing as a
limited liability company, limited partnership or corporation, as the case may be, in good standing under the Laws of its jurisdiction of incorporation or formation, as the case may be, and has the full limited liability company, limited partnership
or corporate, as the case may be, power and authority, and has all governmental licenses, authorizations, consents and approvals, necessary to own, lease or hold its Properties and assets and to conduct the businesses in which it is engaged, and is
duly registered or qualified to do business and in good standing as a foreign limited liability company, limited partnership or corporation, as the case may be, in each jurisdiction in which its ownership or lease of Property or the conduct of its
business requires such qualification, except where the failure to so register or qualify would not reasonably be expected to have a Material Adverse Effect. 

  
 11 

 (b) None of the Partnership Entities is in default in the performance, observance
or fulfillment of any provision of, in the case of the Partnership, the Partnership Agreement or its Certificate of Limited Partnership, in the case of the General Partner, any provision of its certificate of formation or the GP LLC Agreement, or,
in the case of any Subsidiary of the Partnership, its respective certificate of incorporation, certificate of formation, certificate of limited partnership, bylaws, limited liability company agreement, partnership agreement or other similar
organizational documents. 
 (c) The Partnership Agreement has been, and in the case of the Fifth Amended and Restated
Agreement of Limited Partnership, at the Closing will be, duly authorized, executed and delivered by the General Partner and is (or, in the case of the Fifth Amended and Restated Agreement of Limited Partnership, as of the Closing Date will be) a
valid and legally binding agreement of the General Partner, enforceable against the General Partner in accordance with its terms; the GP LLC Agreement (together with the Partnership Agreement, the “Operative Agreements”) has been
duly authorized, executed and delivered by the parties thereto and is a valid and legally binding agreement of the parties thereto, enforceable against the parties thereto in accordance with its terms; provided that, with respect to each Operative
Agreement, the enforceability thereof may be limited by bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and similar laws relating to or affecting creditors’ rights generally and by general principles of equity
(regardless of whether such enforceability is considered in a proceeding in equity or at law); and provided further, that the indemnity, contribution and exoneration provisions contained in any of such Operative Agreements may be limited by
applicable laws and public policy. 
 Section 3.2 Capitalization and Valid Issuance of Purchased Units. 

(a) On the Closing Date, the Purchased Units shall have those rights, preferences, privileges and restrictions governing the
Purchased Units as set forth in the Fifth Amended and Restated Agreement of Limited Partnership. 
 (b) The General Partner
is the sole general partner of the Partnership, with a 2.0% general partner interest in the Partnership (not including any Series A Preferred Units, Series B Preferred Units, Series C Preferred Units, Series D Preferred Units or Warrants); such
general partner interest is the only general partner interest of the Partnership that is issued and outstanding; and such general partner interest has been duly authorized and validly issued and is owned by the General Partner free and clear of any
Liens (except restrictions on transferability contained in the Fifth Amended and Restated Agreement of Limited Partnership). 

  
 12 

 (c) As of the date of this Agreement, prior to and excluding the issuance and
sale of the Purchased Units as contemplated hereby, the issued and outstanding limited partner interests of the Partnership consist of (i) 107,128,349 Common Units, (ii) 6,000,000 of the Partnership’s 7.25% Series A Cumulative
Redeemable Preferred Units (“Series A Preferred Units”), (iii) 5,000,000 of the Partnership’s 8.50% Series B Cumulative Redeemable Preferred Units (“Series B Preferred Units”), (iv) 10,438,413 of the
Partnership’s 8.60% Series C Cumulative Convertible Perpetual Preferred Units (“Series C Preferred Units”) and the (v) Incentive Distribution Rights (as defined in the Partnership Agreement and the Fifth Amended and
Restated Partnership Agreement). All outstanding Common Units, Series A Preferred Units, Series B Preferred Units, Series C Preferred Units and Incentive Distribution Rights and, as applicable, the limited partner interests represented thereby
have been duly authorized and validly issued in accordance with the Partnership Agreement and are fully paid (to the extent required under the Partnership Agreement) and nonassessable (except as such nonassessability may be affected by Sections 30,
41, 51 and 60 of the Marshall Islands LP Act and the Partnership Agreement). Prior to the Closing, the Partnership intends to adopt the Fifth Amended and Restated Partnership Agreement which will, among other things, set forth the rights,
preferences, privileges and restrictions governing the Series D Preferred Units and the Partnership’s Series C-1 Preferred Units to be issued as part of the Partnership’s recapitalization plan. At or about the time of the Closing, the
Partnership will (i) in connection with the Series C Transaction, exchange 1,920,668 Series C Preferred Units for 8,323,809 Common Units, and exchange the remaining 8,517,745 Series C Preferred Units on a one-for-one basis for Series C-1
Preferred Units, and (ii) issue approximately $100 million of Common Units in the Common Unit Offering. 
 (d) The
Series D Preferred Units being purchased by the Purchasers hereunder and the limited partner interests represented thereby will be duly authorized by the Partnership, and, when issued and delivered to the Purchasers against payment therefor in
accordance with the terms of this Agreement, will be validly issued, fully paid (to the extent required by the Fifth Amended and Restated Agreement of Limited Partnership) and nonassessable (except as such nonassessability may be affected by
Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and the Fifth Amended and Restated Agreement of Limited Partnership) and will be free of any and all Liens and restrictions on transfer, other than (i) restrictions on transfer under the
Fifth Amended and Restated Agreement of Limited Partnership, or this Agreement and under applicable state and federal securities laws, (ii) such Liens as are created by the Purchasers and (iii) such Liens as arise under the Fifth Amended
and Restated Agreement of Limited Partnership, or the Marshall Islands LP Act. Except as disclosed in the Partnership SEC Documents, there are no persons entitled to statutory, preemptive or other similar contractual rights to subscribe for the
Purchased Units; and, except for the Purchased Units to be issued pursuant to this Agreement, the Series C Transaction, the Common Unit Offering or as disclosed in the Partnership SEC Documents, no options, warrants or other rights to purchase,
agreements or other obligations to issue, or rights to convert any obligations into or exchange any securities for, partnership securities or ownership interests in the Partnership are outstanding. 

(e) Upon issuance of the Conversion Units or the Warrant Exercise Units in accordance with the terms of the Series D Preferred
Units or Warrants, as applicable, and the Fifth Amended and Restated Agreement of Limited Partnership, the Conversion Units or Warrant Exercise Units, as applicable, will be duly authorized, validly issued, fully paid (to the extent required by the
Fifth Amended and Restated Agreement of Limited Partnership) and nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and the Fifth Amended and Restated Agreement of Limited
Partnership) and will be free of any and all Liens and restrictions on transfer, other than (i) restrictions on transfer under the Basic Documents and under applicable state and federal securities laws, (ii) such Liens as are created by
the Purchasers and (iii) such Liens as arise under the Fifth Amended and Restated Agreement of Limited Partnership or the Marshall Islands LP Act. 

  
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 (f) The Common Units are listed on the NYSE, and the Partnership has not received
any notice of delisting. The issuance and sale of the Purchased Units and the offer of the Conversion Units and Warrant Exercise Units and issuance of such Conversion Units or Warrant Exercise Units upon conversion of the Series D Preferred Units or
exercise of the Warrants, as applicable, following receipt of a countersigned “Supplemental Listing Application” approving the Underlying Units for listing by the NYSE, subject to notice of issuance, does not contravene NYSE rules and
regulations. 
 Section 3.3 Subsidiaries. 

(a) The Partnership owns a 100% membership interest in Teekay Offshore Holdings L.L.C., a Marshall Islands limited liability
company (“Teekay Offshore Holdings”); such membership interest has been duly authorized and validly issued in accordance with the limited liability company agreement of Teekay Offshore Holdings, as amended on or prior to the date
hereof (the “Teekay Offshore Holdings LLC Agreement”), and is fully paid (to the extent required under the Teekay Offshore Holdings LLC Agreement) and nonassessable (except as such nonassessability may be affected by Sections 20,
31, 40 and 49 of the Marshall Islands LLC Act and except as may be provided in the Teekay Offshore Holdings LLC Agreement); and the Partnership owns such membership interest free and clear of all Liens except for Liens pursuant to credit agreements
and related security agreements disclosed or referred to in the Partnership SEC Documents. 
 (b) Teekay Offshore Holdings
owns a 100% membership interest in OLP GP; such membership interest has been duly authorized and validly issued in accordance with the limited liability company agreement of OLP GP, as amended or restated on or prior to the date hereof (the
“OLP GP LLC Agreement”), and is fully paid (to the extent required under the OLP GP LLC Agreement) and nonassessable (except as such nonassessability may be affected by Sections 20, 31, 40 and 49 of the Marshall Islands LLC Act and
the organizational documents of OLP GP); and Teekay Offshore Holdings owns such membership interest free and clear of all Liens except for Liens pursuant to credit agreements and related security agreements disclosed or referred to in the
Partnership SEC Documents. 
 (c) Teekay Offshore Holdings directly owns a 99.09% limited partner interest in the Operating
Company and OLP GP directly owns a 0.91% general partner interest in the Operating Company; such partner interests have been duly authorized and validly issued in accordance with the partnership agreement of the Operating Company, as amended or
restated on or prior to the date hereof (the “Operating Company Partnership Agreement”), and are fully paid (to the extent required under such Operating Company Partnership Agreement) and, with respect to the limited partner
interests, are nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands LP Act and the organizational documents of the Operating Company); and Teekay Offshore Holdings and OLP GP,
respectively, own such partner interests free and clear of all Liens except for Liens pursuant to credit agreements and related security agreements disclosed or referred to in the Partnership SEC Documents. 

  
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 (d) The Partnership and the Operating Company own, directly or indirectly, the
equity interests indicated in such exhibit of the Subsidiaries named in Exhibit 8.1 to the Partnership’s Annual Report on Form 20-F for the year ended December 31, 2015; such equity interests have been duly authorized and validly
issued in accordance with the organizational documents of each Subsidiary, and are fully paid (to the extent required under such organizational documents) and nonassessable (except as such nonassessability may be affected by the applicable statutes
of the jurisdiction of formation of the applicable Subsidiary and the relevant organizational documents); and the Partnership and the Operating Company, as applicable, own such equity interests free and clear of all Liens except for Liens pursuant
to credit agreements and related security agreements disclosed or referred to in the Partnership SEC Documents. 

Section 3.4 No Registration Required. Assuming the accuracy of the representations and warranties of each
Purchaser contained in Article IV, the issuance and sale of the Purchased Units pursuant to this Agreement is exempt from registration requirements of the Securities Act, and neither the Partnership nor, to the knowledge of the Partnership, any
authorized Representative acting on its behalf has taken or will take any action hereafter that would cause the loss of such exemption. 

Section 3.5 No Conflict. None of (i) the offering, issuance and sale by the Partnership of the Purchased
Units and the application of the proceeds therefrom, (ii) the execution, delivery and performance of the Basic Documents by the Partnership, or (iii) the consummation of the transactions contemplated hereby or thereby conflicts or will
conflict with, or results or will result in a breach or violation of or imposition of any Lien upon any Property or assets of the Partnership Entities pursuant to, (A) the formation or governing documents of any of the Partnership Entities,
(B) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which any of the Partnership Entities is a party, by which any of them
is bound or to which any of their respective Properties or assets is subject, or (C) any Law applicable to any of the Partnership Entities or injunction of any court or governmental agency or body to which any of the Partnership Entities of any
court, regulatory body, administrative agency, governmental body, arbitrator or other authority having jurisdiction over any of the Partnership Entities or any of their Properties, except in the case of clause (B) for such conflict, breach,
violation or default that would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

Section 3.6 No Default. None of the Partnership Entities is in violation or default of (i) any provision of
its respective formation or governing documents, (ii) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which it is a party,
by which it is bound or to which its property is subject, or (iii) any Law of any court, regulatory body, administrative agency, governmental body, arbitrator or other authority having jurisdiction over the Partnership Entities or any of their
Properties, as applicable, except, in the case of clauses (ii) or (iii), as would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

  
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 Section 3.7 Authority; Enforceability. The Partnership has all
requisite power and authority to enter into this Agreement. On the Closing Date, the Partnership will have all requisite power and authority to issue, sell and deliver the Purchased Units, in accordance with and upon the terms and conditions set
forth in this Agreement and the Fifth Amended and Restated Agreement of Limited Partnership. On the Closing Date, all partnership or limited liability company action, as the case may be, required to be taken by the General Partner and the
Partnership for the authorization, issuance, sale and delivery of the Purchased Units, the execution and delivery of the Basic Documents and the consummation of the transactions contemplated thereby shall have been validly taken. No approval from
the holders of outstanding Common Units is required under the Fifth Amended and Restated Agreement of Limited Partnership, or the rules of the NYSE in connection with the Partnership’s issuance and sale of the Purchased Units to the Purchasers.
Each of the Basic Documents has been duly and validly authorized and has been or, with respect to the Basic Documents to be delivered at the Closing, will be, validly executed and delivered by the Partnership or the General Partner, as the case may
be, and constitutes, or will constitute, the legal, valid and binding obligations of the Partnership or the General Partner, as the case may be, enforceable in accordance with its terms, except as such enforceability may be limited by bankruptcy,
insolvency, reorganization and other laws of general applicability relating to or affecting creditors’ rights and by general principles of equity, and provided that any indemnity, contribution and exoneration provisions contained in the Basic
Documents may be limited by applicable laws and public policy. 
 Section 3.8 Approvals. Except as required by
the Commission in connection with the Partnership’s obligations under the Registration Rights Agreement, no authorization, consent, approval, waiver, license, qualification or written exemption from, nor any filing, declaration, qualification
or registration with, any Governmental Authority or any other Person is required in connection with the execution, delivery or performance by the Partnership of any of the Basic Documents to which it is a party or the Partnership’s issuance and
sale of the Purchased Units, except (i) as may be required under the state securities or “Blue Sky” Laws, or (ii) where the failure to receive such authorization, consent, approval, waiver, license, qualification or written
exemption or to make such filing, declaration, qualification or registration would not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. 

Section 3.9 Compliance with Laws. Neither the Partnership nor any of its Subsidiaries is in violation of any Law
applicable to the Partnership or its Subsidiaries, except as would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. The Partnership and its Subsidiaries possess all certificates, authorizations and
permits issued by the appropriate regulatory authorities necessary to conduct their respective businesses, except where the failure to possess such certificates, authorizations or permits would not reasonably be expected to have, individually or in
the aggregate, a Material Adverse Effect, and neither the Partnership nor any such Subsidiary has received any notice of proceedings relating to the revocation or modification of any such certificate, authorization or permit, except where such
potential revocation or modification would not reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

  
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 Section 3.10 Periodic Reports. The Partnership’s forms,
registration statements, reports, schedules and statements required to be filed by it under the Exchange Act or the Securities Act (all such documents filed prior to the date hereof, collectively the “Partnership SEC Documents”)
have been filed with the Commission on a timely basis. The Partnership SEC Documents, including any audited or unaudited financial statements and any notes thereto or schedules included therein, at the time filed (or in the case of registration
statements, solely on the dates of effectiveness) (except to the extent corrected by a subsequent Partnership SEC Document) (a) did not contain any untrue statement of a material fact or omit to state a material fact required to be stated
therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading, (b) complied in all material respects with the applicable requirements of the Exchange Act and the
Securities Act, as the case may be, (c) in the case of the financial statements, complied as to form in all material respects with applicable accounting requirements and with the published rules and regulations of the Commission with respect
thereto, (d) in the case of the financial statements, were prepared in accordance with GAAP applied on a consistent basis during the periods involved (except as may be indicated in the notes thereto or, in the case of unaudited statements, for
the absence of certain footnote disclosure and normal, recurring year-end adjustments or as otherwise permitted by the rules and regulations of the Commission), and (e) fairly present (subject in the case of unaudited statements to normal and
recurring audit adjustments) in all material respects the consolidated financial position of the Partnership and its consolidated subsidiaries as of the dates thereof and the consolidated results of its operations and cash flows for the periods then
ended. In addition, the interactive data in eXtensible Business Reporting Language included or incorporated by reference in the Partnership SEC Documents fairly presents the information called for in all material respects and has been prepared in
accordance with the Commission’s rules and guidelines applicable thereto. KPMG LLP is an independent registered public accounting firm with respect to the Partnership and the General Partner and has not resigned or been dismissed as independent
registered public accountants of the Partnership as a result of or in connection with any disagreement with the Partnership on any matter of accounting principles or practices, financial statement disclosure or auditing scope or procedures. 

Section 3.11 Litigation. As of the date hereof, except as set forth on Schedule 3.11 hereto or in the
Partnership SEC Documents, there are no legal or governmental proceedings pending to which any Partnership Entity is a party or to which any Property or asset of any Partnership Entity is subject that would reasonably be expected to have,
individually or in the aggregate, a Material Adverse Effect or which challenges the validity of this Agreement or the right of any Partnership Entity to enter into this Agreement or to consummate the transactions contemplated hereby and, to the
knowledge of the Partnership, no such proceedings are threatened by Governmental Authorities or others. 

Section 3.12 Insurance. The Partnership and its Subsidiaries are insured by insurers of recognized financial
responsibility against such losses and risks and in such amounts as are prudent and customary in the businesses in which they are engaged. The Partnership does not have any reason to believe that it or any Subsidiary will not be able to renew its
existing insurance coverage as and when such coverage expires or to obtain similar coverage from similar insurers as may be necessary to continue its business. 

Section 3.13 Books and Records; Sarbanes Oxley Compliance. 

  
 17 

 (a) The Partnership and its Subsidiaries maintain a system of internal accounting
controls sufficient to provide reasonable assurance that (i) transactions are executed in accordance with management’s general or specific authorizations, (ii) transactions are recorded as necessary to permit preparation of financial
statements in conformity with GAAP and to maintain asset accountability, (iii) access to assets is permitted only in accordance with management’s general or specific authorization, and (iv) the recorded accountability for assets is
compared with the existing assets at reasonable intervals and appropriate action is taken with respect to any differences. The Partnership is not aware of any material weakness in the internal controls over financial reporting of any of the
Partnership Entities. 
 (b) The Partnership has established and maintains disclosure controls and procedures (to the extent
required by and as defined in Rules 13a-15(e) under the Exchange Act, which are designed to provide reasonable assurance that information required to be disclosed by the Partnership in reports that it files or submits under the Exchange Act is
recorded, processed, summarized and communicated to the Partnership’s management, including its principal executive officer and principal financial officer, as appropriate, to allow for timely decisions regarding required disclosure. The
Partnership has carried out evaluations of the effectiveness of its disclosure controls and procedures and such disclosure controls and procedures are effective in all material respects to perform the functions for which they were established. 

(c) There is and has been no failure on the part of the Partnership and, to the Partnership’s knowledge, the General
Partner’s directors or officers, in their capacities as such, to comply in all material respects with all applicable provisions of the Sarbanes-Oxley Act of 2002 and the rules and regulations promulgated in connection therewith. 

Section 3.14 No Material Adverse Changes. As of the date hereof, except as set forth in the Partnership’s
Report on Form 6-K for the quarter ended March 31, 2016, since March 31, 2016, there has been no change, event, occurrence, effect, fact, circumstance or condition that has had or would reasonably be likely to have a Material Adverse
Effect. 
 Section 3.15 Certain Fees. Other than fees payable to Citigroup Global Markets, Inc. and DNB
Markets, Inc. for their services as placement agents, no fees or commissions are or will be payable by the Partnership to brokers, finders, or investment bankers with respect to the sale of any of the Purchased Units or the consummation of the
transactions contemplated by this Agreement. The Partnership agrees that it will indemnify and hold harmless each Purchaser from and against any and all claims, demands, or liabilities for broker’s, finder’s, placement, or other similar
fees or commissions incurred by the Partnership in connection with the sale of the Purchased Units or the consummation of the transactions contemplated by this Agreement. 

Section 3.16 Investment Company Status. The Partnership is not required to be registered as an “investment
company” under the Investment Company Act of 1940, as amended. 
 Section 3.17 Passive Foreign Investment
Company. To the knowledge of the Partnership, after consultation with United States federal income tax counsel, none of the Partnership Entities is a Passive Foreign Investment Company within the meaning of Section 1297 of the Internal
Revenue Code of 1986, as amended. 

  
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 Section 3.18 Tax Status. None of the Partnership Entities, other
than the Partnership and the General Partner, has elected to be classified as an association taxable as a corporation for United States federal income tax purposes. Each of the Partnership Entities, other than the Partnership and the General
Partner, is, or will pursuant to Treasury Regulations Section 301.7701-3 timely and properly elect to be, classified as a disregarded entity if it has one owner or as a partnership if it has more than one owner for United States federal income
tax purposes. 
 Section 3.19 Title to Property. Each of the Partnership Entities has good and marketable title
to all real property and good title to all personal property described in the Partnership SEC Documents as owned by applicable Partnership Entities, free and clear of all Liens except such (i) as are described in the Partnership SEC Documents,
(ii) as do not materially affect the value of such property, taken as a whole, and do not materially interfere with the use of such properties, taken as a whole, as described in the Partnership SEC Documents, or (iii) could not reasonably
be expected, individually or in the aggregate, to have a Material Adverse Effect (the Liens described in clauses (i), (ii) and (iii) above being “Permitted Liens”); provided that with respect to any interest in real
property and buildings held under lease by any Partnership Entity, such real property and buildings are held under valid and subsisting and enforceable leases (except as may be limited by bankruptcy, insolvency, fraudulent transfer, reorganization,
moratorium and similar laws relating to or affecting creditors’ rights generally and by general principles of equity (regardless of whether such enforceability is considered in a proceeding in equity or at law)), with such exceptions as do not
materially interfere with the use of the properties of the Partnership Entities, taken as a whole, as they have been used in the past as described in the Partnership SEC Documents and are proposed to be used in the future, as described in the
Partnership SEC Documents. 
 Section 3.20 No Side Agreements. There are no agreements by, among or between the
Partnership or any of its Affiliates, on the one hand, and any Purchaser (other than any Purchaser that is an Affiliate of the Partnership) or any of their Affiliates, on the other hand, with respect to the transactions contemplated hereby other
than this Agreement, the Registration Rights Agreement and agreements entered into in connection with the Series C Transaction and/or the Common Unit Offering, nor promises or inducements for future transactions between or among any of such parties.

 Section 3.21 Form F-3 Eligibility. As of the Closing Date, the Partnership is eligible to register the
resale of the Series D Preferred Units and the Underlying Units for resale by the Purchasers under Form F-3 promulgated under the Securities Act. 

Section 3.22 Disclosure of Material Information. All documents presented (including the Partnership SEC
Documents) and information provided to the Purchasers or their Representatives by the Partnership, or its Representatives, concerning the Partnership Entities, when taken together as a whole, are complete and accurate in all material respects. All
forecasts and projections provided to the Purchasers were prepared in good faith using reasonable assumptions. 

  
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 Section 3.23 Foreign Corrupt Practices Act. No Partnership Entity,
nor any director, officer, or employee, nor, to the knowledge of the Partnership Entities, any agent or representative of the Partnership Entities, has taken or will take any action, directly or indirectly, that would result in a violation by such
persons of the Foreign Corrupt Practices Act of 1977, as amended (such act, including the rules and regulations thereunder, the “FCPA”), including, making use of the mails or any means or instrumentality of interstate commerce
corruptly in furtherance of an offer, payment, promise to pay, or authorization or approval of the payment or giving of money, property, gifts or anything else of value, directly or indirectly, to any “government official” (including any
officer or employee of a government or government-owned or controlled entity or of a public international organization, or any person acting in an official capacity for or on behalf of any of the foregoing, or any political party or party official
or candidate for political office) to influence official action or secure an improper advantage; and the Partnership Entities have conducted their businesses in compliance with applicable anti-corruption laws and have instituted and maintain and
will continue to maintain policies and procedures designed to promote and achieve compliance with such laws and with the representation and warranty contained herein. 

ARTICLE IV 

REPRESENTATIONS AND WARRANTIES OF THE PURCHASERS 

Each Purchaser, severally and not jointly, hereby represents and warrants to the Partnership that: 

Section 4.1 Existence. Such Purchaser is duly organized and validly existing and in good standing under the Laws
of its jurisdiction of organization, with all requisite power and authority to own, lease, use and operate its Properties and to conduct its business as currently conducted. 

Section 4.2 Authorization, Enforceability. Such Purchaser has all necessary corporate, limited liability company
or partnership power and authority to execute, deliver and perform its obligations under the Basic Documents and to consummate the transactions contemplated thereby, and the execution, delivery and performance by such Purchaser of the Basic
Documents has been duly authorized by all necessary action on the part of such Purchaser; and the Basic Documents, when executed as of the date hereof or prior to the Closing, as applicable, constitute or will constitute the legal, valid and binding
obligations of such Purchaser, enforceable in accordance with its terms, except as such enforceability may be limited by bankruptcy, insolvency, fraudulent transfer and similar laws affecting creditors’ rights generally or by general principles
of equity, including principles of commercial reasonableness, fair dealing and good faith. 
 Section 4.3 No
Breach. The execution, delivery and performance of the Basic Documents by such Purchaser and the consummation by such Purchaser of the transactions contemplated thereby will not (a) conflict with or result in a breach or violation of any of
the terms or provisions of, or constitute a default under, any material agreement to which such Purchaser is a party or by which such Purchaser is bound or to which any of the Property or assets of such Purchaser is subject, (b) conflict with
or result in any violation of the provisions of the organizational documents of such Purchaser, or (c) violate any statute, order, rule or regulation of any court or governmental agency or body having jurisdiction over such Purchaser or the
property or assets of such Purchaser, except in the cases of clauses (a) and (c), for such conflicts, breaches, violations or defaults as would not prevent or delay the consummation of the transactions contemplated by the Basic Documents. 

  
 20 

 Section 4.4 Certain Fees. No fees or commissions are or will be
payable by such Purchaser to brokers, finders, or investment bankers with respect to the purchase of any of the Purchased Units or the consummation of the transaction contemplated by this Agreement. Each Purchaser agrees that it will indemnify and
hold harmless the Partnership from and against any and all claims, demands or liabilities for broker’s, finder’s, placement, or other similar fees or commissions incurred by such Purchaser or alleged to have been incurred by such Purchaser
in connection with the purchase of the Purchased Units or the consummation of the transactions contemplated by this Agreement. 

Section 4.5 Unregistered Securities. 

(a) Such Purchaser is an “accredited investor” within the meaning of Rule 501 under the Securities Act and is able to
bear the risk of its investment in the Series D Preferred Units, the Warrants and the Underlying Units (collectively, the “Securities”). Such Purchaser has such knowledge and experience in financial and business matters that it is
capable of evaluating the merits and risks of the purchase of the Securities. Such Purchaser is a resident for purposes of state “blue sky” securities laws of the jurisdiction set forth on Schedule A attached hereto. 

(b) Such Purchaser understands that the Securities will bear a restrictive legend or legends as provided in the Fifth Amended
and Restated Agreement of Limited Partnership or Warrant Agreement, as applicable, until such legends may be removed pursuant to the Fifth Amended and Restated Agreement of Limited Partnership or Warrant Agreement, as applicable. 

(c) Such Purchaser is purchasing the Purchased Units for its own account and not with a view to distribution in violation of
any securities laws. Such Purchaser has been advised and understands that none of the Securities have been registered under the Securities Act or under the “blue sky” laws of any jurisdiction and may be resold only if registered pursuant
to the provisions of the Securities Act (or if eligible, pursuant to the provisions of Rule 144 promulgated under the Securities Act or pursuant to another available exemption from the registration requirements of the Securities Act). Such Purchaser
has been advised and understands that the Partnership, in issuing the Series D Preferred Units and the Warrants (and any Underlying Units upon conversion or exercise, as applicable, of the Series D Preferred Units and the Warrants), is relying upon,
among other things, the representations and warranties of such Purchaser contained in this Article IV in concluding that such issuance is a “private offering” and is exempt from the registration provisions of the Securities Act.

 (d) Such Purchaser understands that there is no public trading market for the Series D Preferred Units or the Warrants,
that none is expected to develop and that the Series D Preferred Units and the Warrants must be held indefinitely unless and until Series D Preferred Units and the Warrants or any Underlying Units received upon conversion or exercise, as applicable,
thereof are registered under the Securities Act or an exemption from registration is available. Each Purchaser is aware of the provisions of Rule 144 promulgated under the Securities Act. 

  
 21 

 (e) Such Purchaser understands that the Purchased Units are being offered and
sold in reliance on a transactional exemption from the registration requirements of federal and state securities laws and that the Partnership is relying upon the truth and accuracy of the representations, warranties, agreements, acknowledgments and
understandings of such Purchaser set forth herein in order to determine the applicability of such exemptions and the suitability of such Purchaser to acquire the Series D Preferred Units or the Warrants and any Underlying Units issuable upon
conversion or exercise, as applicable, thereof. 
 Section 4.6 No Side Agreements. There are no other
agreements by, among or between such Purchaser (other than any Purchaser that is an Affiliate of the Partnership) and any of its Affiliates, on the one hand, and the Partnership or any of its Affiliates, on the other hand, with respect to the
transactions contemplated hereby other than this Agreement, the Registration Rights Agreement and agreements entered into in connection with the Common Unit Offering and/or the Series C Transaction nor promises or inducements for future transactions
between or among any of such parties; provided, however, that, subject to such Purchaser’s compliance with its obligations under the U.S. federal securities laws and its internal policies: (a) such Purchaser, for purposes hereof, shall not
be deemed to include any employees, subsidiaries or Affiliates that are effectively walled off by appropriate “Chinese Wall” information barriers approved by such Purchaser’s legal or compliance department (and thus have not been
privy to any information concerning this transaction) (a “Walled Off Person”) and (b) the foregoing representations in this paragraph shall not apply to any transaction by or on behalf of such Purchaser that was effected by a
Walled Off Person in the ordinary course of trading without the advice or participation of such Purchaser or receipt of confidential or other information regarding this transaction provided by such Purchaser to such entity. 

Section 4.7 Short Selling. Such Purchaser has not made any trades in the Common Units, Preferred Units or any
other equity interests of the Partnership or entered into or effected any Short Sales of the Common Units owned by it between (a) the earlier of (x) the time it first began discussion with the Partnership about the transactions
contemplated by this Agreement and (y) Friday, June 10, 2016 and (b) June 16, 2016 (it being understood that, without implication that the contrary would otherwise be true, the entering into of a total return swap shall not be
considered a Short Sale of Common Units). Each Purchaser understands and acknowledges, severally and not jointly with any other Purchaser, that the Commission currently takes the position that coverage of short sales of securities “against the
box” prior to the effective date of a registration statement or prior to the time a Purchaser is eligible to sell such securities under Rule 144 is a violation of Section 5 of the Securities Act. 

Section 4.8 Purchaser Investigation; Partnership Projections. Such Purchaser acknowledges and agrees that it has
made its own inquiry and investigation into, and, based thereon, has formed an independent judgment concerning the Partnership and its businesses and operations and prospects, and such Purchaser has been furnished with or given full access to such
information about the Partnership and its businesses and operations as it requested. In connection with such Purchaser’s investigation of the Partnership and its businesses and operations, such Purchaser and its Representatives have received
from the Partnership or its Representatives certain projections and other forecasts for the Partnership and certain estimates, plans and budget information. Such Purchaser acknowledges and agrees that (a) there are uncertainties inherent in
attempting to make such projections, forecasts, estimates, plans and budgets, (b) such Purchaser is familiar with such uncertainties and (c) such Purchaser is taking full responsibility for making its own evaluations of the adequacy and
accuracy of all estimates, projections, forecasts, plans and budgets so furnished to it or its Representatives. 

  
 22 

 ARTICLE V 

COVENANTS 

Section 5.1 Taking of Necessary Action. Each of the parties hereto shall use its commercially reasonable efforts
promptly to take or cause to be taken all action and promptly to do or cause to be done all things necessary, proper or advisable under applicable Law and regulations to consummate and make effective the transactions contemplated by the Basic
Documents. Without limiting the foregoing, the Partnership and each Purchaser shall use its commercially reasonable efforts to make all filings and obtain all consents of Governmental Authorities that may be necessary or, in the reasonable opinion
of the other parties, as the case may be, advisable for the consummation of the transactions contemplated by this Agreement. 

Section 5.2 Other Actions. The Partnership shall, prior to the Closing, file a supplemental listing application
with the NYSE to list the Underlying Units. 
 Section 5.3 Short Sales; Hedging Transactions. Prior to the
first anniversary of the Closing Date, Purchaser shall not, directly or indirectly, engage in any short sales or other derivative or hedging transactions involving the Common Units that are designed to, or that might reasonably be expected to,
result in the transfer to another, in whole or in part, of any of the economic consequences of ownership of any Series D Preferred Units or Warrants. For the avoidance of doubt, this restriction shall also apply to any transferees who receive Series
D Preferred Units prior to the first anniversary of the Closing Date; however, this restriction shall not prohibit any Purchaser from, directly or indirectly, engaging in any short sales or other derivative or hedging transactions involving the
Common Units or other securities of the Partnership held by such Purchaser unrelated to such Purchaser’s Purchased Units. 
 ARTICLE
VI 
 INDEMNIFICATION 

Section 6.1 Indemnification by the Partnership. The Partnership agrees to indemnify each Purchaser and its
Representatives (collectively, “Purchaser Related Parties”) from, and hold each of them harmless against, any and all actions, suits, proceedings (including any investigations, litigation or inquiries), demands, and causes of
action, and, in connection therewith, and promptly upon demand, pay or reimburse each of them for all costs, losses, liabilities, damages, or expenses of any kind or nature whatsoever, including, the reasonable fees and disbursements of counsel and
all other reasonable expenses incurred in connection with investigating, defending or preparing to defend any such matter that may be incurred by them or asserted against or involve any of them as a result of, arising out of, or in any way related
to the breach of any of the representations, warranties or covenants of the Partnership contained herein, provided that such claim for indemnification relating to a breach of the representations or warranties is made prior to the expiration of such
representations or warranties; and provided further, that no Purchaser Related Party shall be entitled to recover special, indirect, incidental, consequential (including lost profits or diminution in value) or punitive damages. Notwithstanding
anything to the contrary, indirect, incidental and consequential damages shall not be deemed to include diminution in value of the Purchased Units to the extent resulting from, arising out of or in any way related to the breach of any of the
representations, warranties or covenants of the Partnership contained herein, which is specifically included in damages covered by the Purchaser Related Parties’ indemnification. 

  
 23 

 Section 6.2 Indemnification by Purchasers. Each Purchaser agrees,
severally and not jointly, to indemnify the Partnership, the General Partner and their respective Representatives (collectively, “Partnership Related Parties”) from, and hold each of them harmless against, any and all actions,
suits, proceedings (including any investigations, litigation or inquiries), demands, and causes of action, and, in connection therewith, and promptly upon demand, pay or reimburse each of them for all costs, losses, liabilities, damages, or expenses
of any kind or nature whatsoever, including, the reasonable fees and disbursements of counsel and all other reasonable expenses incurred in connection with investigating, defending or preparing to defend any such matter that may be incurred by them
or asserted against or involve any of them as a result of, arising out of, or in any way related to the breach of any of the representations, warranties or covenants of such Purchaser contained herein, provided that such claim for indemnification
relating to a breach of the representations and warranties is made prior to the expiration of such representations and warranties; and provided further, that no Partnership Related Party shall be entitled to recover special, indirect, incidental,
consequential (including lost profits or diminution in value) or punitive damages; and provided further, that in no event shall the liability of any Purchaser exceed the amount of such Purchaser’s Purchase Price. 

Section 6.3 Indemnification Procedure. Promptly after any Partnership Related Party or Purchaser Related Party
(hereinafter, the “Indemnified Party”) has received notice of any indemnifiable claim hereunder, or the commencement of any action, suit or proceeding by a third person, which the Indemnified Party believes in good faith is an
indemnifiable claim under this Agreement, the Indemnified Party shall give the indemnitor hereunder (the “Indemnifying Party”) written notice of such claim or the commencement of such action, suit or proceeding, but failure to so
notify the Indemnifying Party will not relieve the Indemnifying Party from any liability it may have to such Indemnified Party hereunder except to the extent that the Indemnifying Party is materially prejudiced by such failure. Such notice shall
state the nature and the basis of such claim to the extent then known. The Indemnifying Party shall have the right to defend and settle, at its own expense and by its own counsel who shall be reasonably acceptable to the Indemnified Party, any such
matter as long as the Indemnifying Party pursues the same diligently and in good faith. If the Indemnifying Party undertakes to defend or settle any such action or claim, it shall promptly notify the Indemnified Party of its intention to do so, and
the Indemnified Party shall cooperate with the Indemnifying Party and its counsel in all commercially reasonable respects in the defense thereof and the settlement thereof. Such cooperation shall include, but shall not be limited to, furnishing the
Indemnifying Party with any books, records and other information reasonably requested by the Indemnifying Party and in the Indemnified Party’s possession or control. Such cooperation of the Indemnified Party shall be at the cost of the
Indemnifying Party. After the Indemnifying Party has notified the Indemnified Party of its intention to undertake to defend or settle any such asserted liability, and for so long as the Indemnifying Party diligently pursues such defense, the
Indemnifying Party shall not be liable for any additional legal expenses incurred by the Indemnified Party in connection with any defense or settlement of such asserted liability; provided, however, that the Indemnified Party shall be entitled
(i) at its expense, to participate in the defense of such asserted liability and the negotiations of the settlement thereof and (ii) if (A) the Indemnifying Party has failed to assume the defense or employ counsel reasonably
acceptable to the Indemnified Party or (B) if the defendants in any such action include both the Indemnified Party and the Indemnifying Party and counsel to the Indemnified Party shall have concluded that there may be reasonable defenses
available to the Indemnified Party that are different from or in addition to those available to the Indemnifying Party or if the interests of the Indemnified Party reasonably may be deemed to conflict with the interests of the Indemnifying Party,
then the Indemnified Party shall have the right to select a separate counsel and to assume such legal defense and otherwise to participate in the defense of such action, with the expenses and fees of such separate counsel and other expenses related
to such participation to be reimbursed by the Indemnifying Party as incurred. Notwithstanding any other provision of this Agreement, the Indemnifying Party shall not settle any indemnified claim without the consent of the Indemnified Party, unless
the settlement thereof imposes no liability or obligation on, includes a complete release from liability of, and does not include any admission of wrongdoing or malfeasance by, the Indemnified Party. 

  
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 ARTICLE VII 

MISCELLANEOUS 

Section 7.1 Expenses. Except as follows, all costs and expenses, including fees and disbursements of counsel, financial
advisors and accountants, incurred in connection with the Basic Documents and the transactions contemplated thereby shall be paid by the party incurring such costs and expenses: 

Promptly following receipt of an invoice therefore containing reasonable supporting detail, the Partnership shall reimburse
the Purchasers for the reasonable fees and expenses of Kirkland & Ellis LLP, counsel to the Purchasers, of up to $250,000 (with legal fees and expenses of Kirkland & Ellis LLP in excess of $250,000 to be paid pro rata by all the
Purchasers in proportion to the aggregate number of Purchased Units purchased by each). 
 Section 7.2
Interpretation. Article, Section, Schedule, and Exhibit references are to this Agreement, unless otherwise specified. All references to instruments, documents, contracts, and agreements are references to such instruments, documents,
contracts, and agreements as the same may be amended, supplemented, and otherwise modified from time to time, unless otherwise specified. The word “including” shall mean “including but not limited to.” Whenever any party has an
obligation under this Agreement, the expense of complying with that obligation shall be an expense of such party unless otherwise specified herein. Whenever any determination, consent, or approval is to be made or given by any party under this
Agreement, such action shall be in such party’s sole discretion unless otherwise specified herein. If any provision in this Agreement is held to be illegal, invalid, not binding, or unenforceable, (i) such provision shall be fully
severable and this Agreement shall be construed and enforced as if such illegal, invalid, not binding, or unenforceable provision had never comprised a part of this Agreement, and the remaining provisions shall remain in full force and effect and
(ii) the parties thereto shall negotiate in good faith to modify this Agreement so as to effect the original intent of the parties as closely as possible in an acceptable manner in order that the transactions contemplated hereby are consummated
as originally contemplated to the greatest extent possible. When calculating the period of time before which, within which or following which any act is to be done or step taken pursuant to this Agreement, the date that is the reference date in
calculating such period shall be excluded. If the last day of such period is a non-Business Day, the period in question shall end on the next succeeding Business Day. Any words imparting the singular number only shall include the plural and vice
versa. The words such as “herein,” “hereinafter,” “hereof” and “hereunder” refer to this Agreement as a whole and not merely to a subdivision in which such words appear unless the context otherwise requires.
The provision of a Table of Contents, the division of this Agreement into Articles, Sections and other subdivisions and the insertion of headings are for convenience of reference only and shall not affect or be utilized in construing or interpreting
this Agreement. This Agreement has been reviewed and negotiated by sophisticated parties with access to legal counsel and shall not be construed against the drafter. 

  
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 Section 7.3 Survival of Provisions. The representations and
warranties set forth in Sections 3.1, 3.2, 3.7, 3.15, 4.1, 4.2, 4.4, 4.5, 4.6 and 4.8 hereunder shall survive the execution and delivery of this Agreement indefinitely, and the other representations and warranties set forth herein shall survive
for a period of twelve (12) months following the Closing Date regardless of any investigation made by or on behalf of the Partnership or any Purchaser. The covenants and agreements made in this Agreement, including the covenants and agreements
set forth in this Article VII, shall, unless otherwise specified therein, survive the Closing of the transactions described herein and remain operative and in full force and effect regardless of acceptance of any of the Purchased Units and payment
therefor and repayment, conversion, exercise or repurchase thereof. All indemnification obligations of the Partnership and the Purchasers pursuant to this Agreement and the provisions of Article VI shall remain operative and in full force and effect
unless such obligations are expressly terminated in a writing by the parties, regardless of any purported general termination of this Agreement. 

Section 7.4 No Waiver; Modifications in Writing. 

(a) No failure or delay on the part of any party in exercising any right, power, or remedy hereunder shall operate as a waiver
thereof, nor shall any single or partial exercise of any such right, power, or remedy preclude any other or further exercise thereof or the exercise of any other right, power, or remedy. The remedies provided for herein are cumulative and are not
exclusive of any remedies that may be available to a party at law or in equity or otherwise. 
 (b) Except as otherwise
provided herein, no amendment, waiver, consent, modification, or termination of any provision of this Agreement shall be effective unless signed by each of the parties thereto affected by such amendment, waiver, modification or termination. Any
amendment, supplement or modification of or to any provision of this Agreement, any waiver of any provision of this Agreement, and any consent to any departure by the Partnership or any Purchaser from the terms of any provision of this Agreement
shall be effective only in the specific instance and for the specific purpose for which made or given. Except where notice is specifically required by this Agreement, no notice to or demand on the Partnership or any Purchaser in any case shall
entitle the Partnership or such Purchaser to any other or further notice or demand in similar or other circumstances. 

  
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 Section 7.5 Binding Effect; Assignment. 

(a) This Agreement shall be binding upon the Partnership, the Purchasers, and their respective successors and permitted
assigns. Except as expressly provided in this Agreement, this Agreement shall not be construed so as to confer any right or benefit upon any Person other than the parties to this Agreement and their respective successors and permitted assigns. 

(b) All or any portion of the rights and obligations of any Purchaser under this Agreement may be transferred by such Purchaser
to any Affiliate of such Purchaser without the consent of the Partnership. No portion of the rights and obligations of any Purchaser under this Agreement may be transferred by such Purchaser to a non-Affiliate without the prior written consent of
the Partnership (which consent shall not be unreasonably withheld by the Partnership). As a condition to any assignment hereunder, the assignee shall agree in writing to be bound by the provisions of this Agreement, and, notwithstanding any such
assignment, the Purchaser shall remain liable for the payment of the Purchase Price of the applicable Purchased Units if not timely paid by such assignee. The Partnership may not transfer any of its rights or obligations under this Agreement to any
Person. 
 Section 7.6 Disclosure. 

(a) The Partnership Entities and any of their respective Representatives shall disclose the identity of, or any other
information concerning the Purchasers or any of their respective Affiliates only after providing the Purchasers a reasonable opportunity to review and comment on such disclosure (with such comments being incorporated or reflected, to the extent
reasonable, in any such disclosure); provided, however, that nothing in this Section 7.6 shall delay any required filing or other disclosure with the Commission, NYSE or any Governmental Authority or otherwise hinder the Partnership
Entities’ or their Representatives’ ability to timely comply with all laws or rules and regulations of the Commission, NYSE or other Governmental Authority. 

(b) Notwithstanding anything to the contrary in this Section 7.6, the Partnership and the General Partner agree
that the Purchasers may, (i) publicize in its marketing materials that the Purchaser acted as “Purchaser” in connection with the Purchased Units (which may include the reproduction of the Partnership’s logos) and, (ii) with
respect to any marketing material distributed to a Purchasers’ Affiliates or funds managed or advised by a Purchaser or investors or potential investors of such funds, the Purchasers may disclose general information (including the size of the
Purchaser’s investment and pricing terms) that is customary for such client or fund raising marketing. 

Section 7.7 Communications. All notices and demands provided for hereunder shall be in writing and shall be given
by registered or certified mail, return receipt requested, telecopy, air courier guaranteeing overnight delivery or personal delivery to the following addresses: 

(a) If to any Purchaser: 

To its respective address listed on Schedule B hereof 

  
 27 

 with a copy (which shall not constitute notice) to: 

Kirkland & Ellis LLP 

600 Travis St., Suite 3300 

Houston, Texas 77002 

Attention: Matthew R. Pacey 

Facsimile: (713) 835-3601 

Email: matt.pacey@kirkland.com 

(b) If to the Partnership: 

Teekay Offshore Partners L.P. 

4th Floor, Belvedere Building 

69 Pitts Bay Road 

Hamilton HM 08, Bermuda 

Attention: Corporate Secretary 

Facsimile: (441) 292-3931 

with a copy (which shall not constitute notice) to: 

Perkins Coie LLP 

1120 N.W. Couch Street, 10th Floor 

Portland, Oregon 97209-4128 

Attention: David Matheson 

Facsimile: (503) 346-2008 

or to such other address as the Partnership or such Purchaser may designate in writing. All notices and communications shall be deemed to have
been duly given: at the time delivered by hand, if personally delivered, at the time of transmittal; if sent via electronic mail; upon actual receipt if sent by certified mail, return receipt requested, or regular mail, if mailed; when receipt
acknowledged, if sent via facsimile; and upon actual receipt when delivered to an air courier guaranteeing overnight delivery. 

Section 7.8 Entire Agreement. This Agreement, the other Basic Documents and the other agreements and documents
referred to herein are intended by the parties as a final expression of their agreement and intended to be a complete and exclusive statement of the agreement and understanding of the parties hereto and thereto in respect of the subject matter
contained herein and therein. There are no restrictions, promises, warranties or undertakings, other than those set forth or referred to herein or the other Basic Documents with respect to the rights granted by the Partnership or any of its
Affiliates or any Purchaser or any of its Affiliates set forth herein. This Agreement, the other Basic Documents and the other agreements and documents referred to herein or therein supersede all prior agreements and understandings between the
parties with respect to such subject matter. 

  
 28 

 Section 7.9 Removal of Legend. In connection with a sale of the
Series D Preferred Units by a Purchaser in reliance on Rule 144, the applicable Purchaser or its broker shall deliver to the Partnership a broker representation letter providing to the Partnership any information the Partnership deems necessary to
determine that the sale of the Series D Preferred Units is made in compliance with Rule 144, including, as may be appropriate, a certification that the Purchaser is not an Affiliate of the Partnership and regarding the length of time the Series D
Preferred Units have been held. After a registration statement under the Securities Act permitting the public resale of the Series D Preferred Units has become effective or any Purchaser or its permitted assigns have held the Series D Preferred
Units for six months, if the certificate for such Series D Preferred Units or the book-entry account of such Series D Preferred Units still bears the notation of the restrictive legend referred to in Section 4.5, the Partnership agrees,
upon request of the Purchaser or permitted assignee, to take all steps reasonably necessary to promptly effect the removal of the legend from the Series D Preferred Units, and the Partnership shall bear all costs associated therewith, regardless of
whether the request is made in connection with a sale or otherwise, so long as such Purchaser or its permitted assigns provide to the Partnership any information the Partnership deems necessary to determine that the legend is no longer required
under the Securities Act or applicable state laws, including (if there is no such registration statement) a certification that the holder is not an Affiliate of the Partnership (and a covenant to inform the Partnership if it should thereafter become
an Affiliate and to consent to exchange its certificates for certificates bearing an appropriate restrictive legend) and regarding the length of time the Series D Preferred Units have been held. Assuming a registration statement is effective or the
Series D Preferred Units have been held for greater than six months, whether held in certificated form or in book entry with the transfer agent, the Partnership agrees that upon request, it shall cooperate with the Purchaser to have the Series D
Preferred Units moved to such Purchaser’s DTC custodial or brokerage account according to the instructions provided by such Purchaser. 

Section 7.10 Governing Law. This Agreement will be construed in accordance with and governed by the laws of the
State of New York without regard to principles of conflicts laws thereof that would apply the laws of any other jurisdiction. 

Section 7.11 Execution in Counterparts. This Agreement may be executed in any number of counterparts and by
different parties hereto in separate counterparts, including facsimile or .pdf format counterparts, each of which counterparts, when so executed and delivered, shall be deemed to be an original and all of which counterparts, taken together, shall
constitute but one and the same Agreement. 
 Section 7.12 Termination. 

(a) Notwithstanding anything herein to the contrary, this Agreement may be terminated at any time at or prior to the Closing by
(i) with respect to any particular Purchaser, the written notice by such Purchaser to the Partnership, upon a breach in any material respect by the Partnership of any covenant or agreement set forth in this Agreement or (ii) with respect
to any particular Purchaser, written notice by the Partnership to such Purchaser upon a breach in any material respect by such Purchaser of any covenant or agreement set forth in this Agreement. For the avoidance of doubt, the termination of this
Agreement with respect to any particular Purchaser shall not affect the Agreement with respect to any other Purchaser. 
 (b)
Notwithstanding anything herein to the contrary, this Agreement shall automatically terminate (i) at any time at or prior to the Closing if a statute, rule, order, decree or regulation shall have been enacted or promulgated, or if any action
shall have been taken by any Governmental Authority of competent jurisdiction that permanently restrains, permanently precludes, permanently enjoins or otherwise permanently prohibits the consummation of the transactions contemplated by this
Agreement or makes the transactions contemplated by this Agreement illegal or (ii) if the Closing shall not have occurred by July 15, 2016. 

  
 29 

 (c) In the event of the termination of this Agreement as provided in this
Section 7.12, (1) this Agreement shall forthwith become null and void as to the applicable parties, and (2) there shall be no liability on the part of such Parties hereto, except as set forth in Article VI of this
Agreement; provided, however, that nothing herein shall relieve any Party from any liability or obligation with respect to any willful breach of this Agreement. 

Section 7.13 Recapitalization, Exchanges, Etc. Affecting the Common Units. The provisions of this Agreement shall
apply to the full extent set forth herein with respect to any and all equity interests of the Partnership or any successor or assign of the Partnership (whether by merger, consolidation, sale of assets or otherwise) which may be issued in respect
of, in exchange for or in substitution of, the Common Units, and shall be appropriately adjusted for combinations, recapitalizations and the like occurring after the date of this Agreement and prior to the Closing. 

[Signature pages follow] 

  
 30 

 IN WITNESS WHEREOF, the parties hereto execute this Agreement, effective as of
the date first above written. 
  

			
	TEEKAY OFFSHORE PARTNERS L.P.
		
	 By:
	 	 TEEKAY OFFSHORE GP L.L.C.

		 	 (its General Partner)

		
	 By:
	 	 /s/ Peter Evensen

		 	  

		 	 Name: Peter Evensen

		 	 Title: Chief Executive Officer and Chief Financial Officer

 
			
	PURCHASER:
	
	CONCORD EQUITY (CAYMAN) LIMITED
		
	 By:
	 	 /s/ Diane C. Bowe-Pindling

		 	  

	 Name:
	 	 Diane C. Bowe-Pindling

	 Title:
	 	 Director

 
			
	PURCHASER:
	
	RESOLUTE INVESTMENTS, LTD.
		
	 By:
	 	 /s/ Cora Lee Starzomski

		 	  

	 Name:
	 	 Cora Lee Starzomski

	 Title:
	 	 Director

 
			
	 PURCHASER:

	
	 TEEKAY CORPORATION

		
	 By:
	 	 /s/ Peter Evensen

		 	  

	 Name:
	 	 Peter Evensen

	 Title:
	 	 President and Chief Executive Officer

 
	
	PURCHASER:
	
	 /s/ Peter Evensen

	 Name: Peter Evensen

 
			
	PURCHASER:
	
	MTP ENERGY FUND LTD
		
	 By:
	 	 MTP Energy Management LLC, its Investment Advisor

	 By:
	 	 Magnetar Financial LLC, its Sole Member

		
	 By:
	 	 /s/ Michael Turro

	 Name:
	 	 Michael Turro

	 Title:
	 	 Chief Compliance Officer

 
			
	PURCHASERS:
	
	TRIANGLE PEAK PARTNERS II, LP
		
	 By:
	 	Triangle Peak Partners II General Partner, LLC, its General Partner
		
	 By:
	 	 /s/ Michael C. Morgan

		 	  

	 Name:
	 	 Michael C. Morgan

	 Title:
	 	 Manager

	
	TPP II ANNEX FUND, LP
		
	 By:
	 	Triangle Peak Partners II General Partner, LLC, its General Partner
		
	 By:
	 	 /s/ Michael C. Morgan

		 	  

	 Name:
	 	 Michael C. Morgan

	 Title:
	 	 Manager

 
			
	PURCHASERS:
	
	COBALT PARTNERS, LP
		
	 By:
	 	 Cobalt Management, LLC, its general partner

		
	 By:
	 	 /s/ Wayne Cooperman

		 	  

	 Name:
	 	 Wayne Cooperman

	 Title:
	 	 Managing Member

	
	COBALT OFFSHORE MASTER FUND, LP
		
	 By:
	 	 Cobalt Management, LLC, its general partner

		
	 By:
	 	 /s/ Wayne Cooperman

		 	  

	 Name:
	 	 Wayne Cooperman

	 Title:
	 	 Managing Member

	
	COBALT PARTNERS II, LP
		
	 By:
	 	 Cobalt Management, LLC, its general partner

		
	 By:
	 	 /s/ Wayne Cooperman

		 	  

	 Name:
	 	 Wayne Cooperman

	 Title:
	 	 Managing Member

	
	COBALT KC PARTNERS, LP
		
	 By:
	 	 Cobalt Management, LLC, its general partner

		
	 By:
	 	 /s/ Wayne Cooperman

		 	  

	 Name:
	 	 Wayne Cooperman

	 Title:
	 	 Managing Member

 
			
	PURCHASER:
	
	LUMINUS ENERGY PARTNERS MASTER FUND, LTD.
		
	 By:
	 	 Luminus Management, LLC

	 Its:
	 	 Investment Manager

		
	 By:
	 	 /s/ Jeffrey Wade

		 	  

	 Name:
	 	 Jeffrey Wade

	 Title:
	 	 General Counsel

 
			
	PURCHASERS:
	
	BROOKFIELD GLOBAL INFRASTRUCTURE SECURITIES INCOME FUND
		
	 By:
	 	 Brookfield Investment Management Inc., its

		 	 Investment Manager

		
	 By:
	 	 /s/ Seth Gelman

		 	  

	 Name:
	 	 Seth Gelman

	 Title:
	 	 Chief Compliance Officer

	
	PURCHASERS:
	
	BROOKFIELD GLOBAL LISTED INFRASTRUCTURE INCOME FUND INC.
		
	 By:
	 	 Brookfield Investment Management Inc., its

		 	 Investment Manager

		
	 By:
	 	 /s/ Seth Gelman

		 	  

	 Name:
	 	 Seth Gelman

	 Title:
	 	 Chief Compliance Officer

 
			
	
	PURCHASER:
	
	DNB Bank ASA
		
	 By:
	 	 /s/ Peter Behncke

		 	  

	 Name:
	 	 Peter Behncke

	 Title:
	 	 Global Head Investment Banking

 Schedule A – List of Purchasers and Commitment Amounts 

 

																	
	 Purchaser
	  	Series D
Preferred
Units	 	  	Series A
Warrants	 	  	Series B
Warrants	 	  	Purchase Price*	 
	 Concord Equity (Cayman) Limited
	  	 	160,000	  	  	 	180,000	  	  	 	90,000	  	  	$	4,000,000.00	  
	 Resolute Investments, Ltd.
	  	 	440,000	  	  	 	495,000	  	  	 	247,500	  	  	$	11,000,000.00	  
	 Teekay Corporation
	  	 	1,040,000	  	  	 	1,170,000	  	  	 	585,000	  	  	$	26,000,000.00	  
	 Peter Evensen
	  	 	20,000	  	  	 	22,500	  	  	 	11,250	  	  	$	500,000.00	  
	 MTP Energy Fund Ltd
	  	 	936,000	  	  	 	1,053,000	  	  	 	526,500	  	  	$	23,400,000.00	  
	 Triangle Peak Partners II, LP
	  	 	12,000	  	  	 	13,500	  	  	 	6,750	  	  	$	300,000.00	  
	 TPP II Annex Fund, LP
	  	 	52,000	  	  	 	58,500	  	  	 	29,250	  	  	$	1,300,000.00	  
	 Cobalt Partners II, LP
	  	 	44,000	  	  	 	49,500	  	  	 	24,750	  	  	$	1,100,000.00	  
	 Cobalt Offshore Master Fund, LP
	  	 	92,000	  	  	 	103,500	  	  	 	51,750	  	  	$	2,300,000.00	  
	 Cobalt Partners, LP
	  	 	334,000	  	  	 	375,750	  	  	 	187,875	  	  	$	8,350,000.00	  
	 Cobalt KC Partners, LP
	  	 	30,000	  	  	 	33,750	  	  	 	16,875	  	  	$	750,000.00	  
	 DNB Bank ASA
	  	 	400,000	  	  	 	450,000	  	  	 	225,000	  	  	$	10,000,000.00	  
	 Brookfield Global Infrastructure Securities Income Fund
	  	 	154,425	  	  	 	173,728	  	  	 	86,864	  	  	$	3,860,625.00	  
	 Brookfield Global Listed Infrastructure Income Fund Inc.
	  	 	245,575	  	  	 	276,272	  	  	 	138,136	  	  	$	6,139,375.00	  
	 Luminus Energy Partners Master Fund, Ltd.
	  	 	40,000	  	  	 	45,000	  	  	 	22,500	  	  	$	1,000,000.00	  
		  	  
	  
	 	  	  
	  
	 	  	  
	  
	 	  	  
	  
	 
	 Total
	  	 	4,000,000	  	  	 	4,500,000	  	  	 	2,250,000	  	  	$	100,000,000.00	  
		  	  
	  
	 	  	  
	  
	 	  	  
	  
	 	  	  
	  
	 

  

	*	The Purchase Price for each Purchaser is equal to the product of (i) the number of Series D Preferred Units set forth opposite such Purchaser’s name under the column titled “Series D Preferred
Units”, multiplied by (ii) the Purchased Unit Price ($25.00 per Purchased Unit). 

 Schedule 3.11 

Litigation 
 See
Item 1 - Financial Statements: Note 10(h) and (i) - Commitments and Contingencies, in the Partnership’s Form 6-K for the quarter ended March 31, 2016. 

 Exhibit A – Form of Warrant Agreement 

 Exhibit B – Form of Opinion of Perkins Coie LLP 

 

	i.	 To our knowledge, except as contemplated by the Series C Transaction, the Common Unit Offering and as
described in the Partnership SEC Documents filed prior to the date of the Purchase Agreement, there are no outstanding options, warrants, or agreements for the purchase or acquisition from the Partnership of Partnership securities or ownership
interests in the Partnership, or rights to convert any obligations into or exchange any securities for Partnership securities or ownership interests in the Partnership. 

 

	ii.	 All consents, approvals, authorizations or other orders of, or registrations or filings on the part of the
Partnership with, any United States federal or New York governmental or regulatory authority required for the Partnership’s execution and delivery of the Transaction Documents and the consummation of the Transactions, including the offering,
issuance and sale of the Series D Preferred Units and the Warrants, have been made or obtained, other than (a) those required by the Commission in connection with the Partnership’s obligations under the Registration Rights Agreement and
(b) those that have been obtained or as may be required under state securities or “Blue Sky” laws, as to which we do not express any opinion. 

  

	iii.	 To our knowledge, there are no contracts, agreements or understandings between any of the Teekay Entities and
any person granting such person the right to require any of the Teekay Entities to file a registration statement under the Act with respect to any securities of the Partnership owned or to be owned by such person or to require any of the Teekay
Entities to include such securities in any securities being registered pursuant to any other registration statement filed by any Teekay Entity under the Act, except for the Registration Rights Agreement, the Common Unit Registration Rights
Agreement, the Existing Registration Rights Agreements, and any such rights held by the General Partner or an Affiliate (as defined in the Partnership Agreement) of the General Partner pursuant to the Partnership Agreement. 

 

	iv.	 The Partnership’s offering, issuance and sale of the Series D Preferred Units and the Warrants and the
Partnership’s execution and delivery of the Transaction Documents and consummation of the Transactions do not (i) breach or result in a default under (or constitute an event which, with notice or lapse of time or both, would constitute
such a default) any Material Agreement, or (ii) violate statutory U.S. federal laws or the laws of the State of New York that counsel exercising customary professional judgment would in our experience reasonably recognize as typically
applicable to agreements similar to the Transaction Documents and the Transactions. “Material Agreement” means any indenture, contract, mortgage, deed of trust, note agreement, loan agreement, lease or other agreement or instrument filed
by the Partnership as an exhibit to the Partnership’s Annual Report on Form 20-F for the year ended December 31, 2015, filed with the Commission on April 18, 2016. 

 

	v.	 Assuming the Transaction Documents have been duly authorized, executed and delivered by the Partnership, each
of the Transaction Documents will constitute a valid and legally binding agreement of the Partnership, enforceable against the Partnership in accordance with its terms. 

	vi.	 Based in part upon the Partnership’s and the Purchasers’ representations and warranties in, and on
the facts and circumstances contemplated by, the Purchase Agreement, the offer, issuance and sale of the Series D Preferred Units, Conversion Units and the Warrants by the Partnership to the Purchasers pursuant to the terms of the Purchase
Agreement, do not require registration under Section 5 of the Securities Act. (We do not comment or opine as to any subsequent sale of the Purchased Units, Warrants or Warrant Exercise Units.) 

 

	vii.	 The Partnership is not, and immediately after giving effect to the use of proceeds from the sale of the Series
D Preferred Units and the Warrants pursuant to the Purchase Agreement will not be, required to register as an “investment company” under the Investment Company Act of 1940, as amended. 

 Exhibit C – Form of Opinion of Watson Farley & Williams LLP 

 

	1.	 Each of the Partnership and the Operating Company has been duly formed and is validly existing in good
standing as a limited partnership under Marshall Islands Law, and has the limited partnership power and authority to own or lease its properties and to conduct its business, in each case in all material respects as described in the
Partnership’s reports and statements filed or furnished by it with the Securities and Exchange Commission (the “SEC Documents”). 

  

	2.	 Each of the General Partner and the OLP GP has been duly formed and is validly existing in good standing as a
limited liability company under Marshall Islands Law, and each has the limited liability company power and authority to own or lease its properties and to conduct its business, in each case in all material respects as described in the SEC Documents.

  

	3.	 Each of the Marshall Islands Significant Subsidiaries is validly existing in good standing as a limited
liability company or corporation, as applicable, under Marshall Islands Law, and each has the limited liability company or corporate power, as applicable, and authority to own or lease its properties and to conduct its business, in each case in all
material respects as described in the SEC Documents. 

  

	4.	 The Units to be issued and sold pursuant to the Purchase Agreement and the limited partner interests
represented thereby have been duly authorized in accordance with the Partnership Agreement and, when issued and delivered to the purchaser thereof against payment therefor in accordance with the terms of the Purchase Agreement, will be validly
issued, fully paid (to the extent required under the Partnership Agreement) and nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands Limited Partnership Act and except as may otherwise
be provided in the Partnership Agreement). 

  

	5.	 The Warrant Units to be issued and sold pursuant to the exercise of the Warrants, when issued against payment
therefor in accordance with the terms and conditions of the relevant Warrant, have been duly authorized in accordance with the Partnership Agreement and, when issued and delivered to the purchaser thereof against payment therefor in accordance with
the terms of the relevant Warrant, will be validly issued, fully paid (to the extent required under the Partnership Agreement) and nonassessable (except as such nonassessability may be affected by Sections 30, 41, 51 and 60 of the Marshall Islands
Limited Partnership Act and except as may otherwise be provided in the Partnership Agreement), assuming no relevant change in applicable law after the date hereof. 

 

	6.	 Except as described in the SEC Documents, and except as contained in Articles V, VII, XI, XV and XVI of the
Partnership Agreement, the Partnership Agreement does not contain any preemptive rights or other rights to subscribe for or to purchase any limited partner interests in the Partnership. 

	7.	 The execution, delivery and performance of the Purchase Agreement and the Warrants, and the consummation of
the transactions contemplated thereby, including the offering, issuance and sale by the Partnership of the Units and the Warrant Units in accordance with and upon the terms and conditions set forth in the Purchase Agreement and the Warrants, do not
(i) conflict with or constitute a violation of the organizational documents of any of the Teekay Parties or the Marshall Islands Significant Subsidiaries, (ii) conflict with or constitute a breach or violation of, or a default under (or an
event which, with notice or lapse of time or both, would constitute such a default), the Teekay Offshore Partners L.P. 2006 Long-Term Incentive Plan, (iii) violate Marshall Islands Law, or (iv) violate any judgment, order or decree of
which we are aware of any court, regulatory body, administrative agency, governmental body, arbitrator or other authority situated in the Republic of the Marshall Islands directed to any of the Teekay Parties or the Marshall Islands Significant
Subsidiaries in a proceeding before such court, regulatory body, administrative agency, governmental body, arbitrator or other authority in the Republic of the Marshall Islands to which any of them is a party. 

 

	8.	 No permit, consent, approval, authorization, order, registration, filing or qualification of or with any
court, governmental agency or body of the Republic of the Marshall Islands having jurisdiction over the Teekay Parties or any of the Marshall Islands Significant Subsidiaries or any of their respective properties is required in connection with the
execution and delivery of the Purchase Agreement or the Warrants by the General Partner in its capacity as the general partner of the Partnership, the performance of the transactions contemplated thereby by the Partnership or the performance by the
Partnership of its obligations thereunder, including the offering, issuance and sale by the Partnership of the Units and Warrant Units in accordance with and upon the terms and conditions set forth in the Purchase Agreement and the Warrants.

  

	9.	 The choice of New York law to govern the Purchase Agreement and the Registration Rights Agreement, and the
Warrants constitutes a valid choice of law under Marshall Islands Law. 

  

	10.	 Each of the Purchase Agreement, the Registration Rights Agreement, and the Warrants has been duly authorized
and validly executed and delivered by the Partnership. 

 Exhibit D – Form of General Partner Waiver 

June 29, 2016 

Teekay Offshore GP L.L.C. (the “General Partner”), a Marshall Islands limited liability company and the
general partner of Teekay Offshore Partners L.P. (the “Partnership”), in its own capacity and in its capacity as the general partner of the Partnership, hereby waives any preemptive rights it may hold pursuant to Section 5.7 of the
Fourth Amended and Restated Agreement of Limited Partnership of the Partnership, dated as of July 1, 2015, as amended, with respect to: 
  

	 	(1)	 the Partnership’s privately-negotiated Series D Preferred Unit and Warrant Purchase Agreement, dated as
of June 22, 2016, by and among the Partnership and each of the purchasers set forth in Schedule A thereto, to issue and sell an aggregate of 4,000,000 Series D Preferred Units representing limited partner interests of the Partnership and warrants
exercisable into 6,750,000 Common Units representing limited partner interests of the Partnership, for an aggregate purchase price of $100,000,000; 

  

	 	(2)	 the Partnership’s privately-negotiated Common Unit Purchase Agreement, dated as of June 16, 2016, by and
among the Partnership and each of the purchasers set forth in Schedule A thereto, to issue and sell an aggregate of 21,978,022 Common Units representing limited partner interests of the Partnership for an aggregate purchase price of $100,000,000.40;
and 

  

	 	(3)	 the Letter Agreement, dated as of June 2, 2016, as amended, between the Partnership and the holders of the
Series C Preferred Units set forth in Schedule A thereto, setting forth the terms of (i) the exchange of 1,920,668 Series C Preferred Units representing limited partner interests of the Partnership 8,323,810 Common Units representing limited partner
interests of the Partnership, and (ii) the exchange 8,517,745 Series C Preferred Units representing limited partner interests of the Company for 8,517,745 Series C-1 Preferred Units representing limited partner interests of the Company.

  

			
	 TEEKAY OFFSHORE GP L.L.C.

	
	By: /s/ 
Peter Evensen                                      
          
	 Name: Peter Evensen

	Title: Chief Executive Officer and Chief Financial Officer

 Exhibit E – Form of Fifth Amended and Restated Agreement of Limited Partnership 

 Exhibit F – Form of Registration Rights Agreement

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