Exhibit 4.9
 This OPCO Limited Partner Interest Purchase Agreement is made effective as of
March 8, 2011
 BETWEEN
    
    Teekay Holdings Limited, a Bermuda company having an office at 4th Floor, Belvedere
Building, 69 Pitts Bay Road, Hamilton, HM 08, Bermuda (THL);AND
    
    Teekay Offshore Partners L.P., a Marshall Islands limited partnership having an office
at 4th Floor, Belvedere Building, 69 Pitts Bay Road, Hamilton, HM 08, Bermuda (Teekay
Offshore).WHEREAS
    
    THL owns 49.0% of the limited partner interests in Teekay Offshore Operating L.P.
(OPCO);AND
    
    Teekay Offshore owns a 50.99% limited partner interest and, indirectly, a 0.01% general
partner interest in OPCO;AND
    
    Teekay Offshore wishes to purchase from THL, and THL wishes to sell to Teekay Offshore,
THLs 49% of the limited partner interests in OPCO.
  1.
    
    INTERPRETATION
 1.1
    
    In this Agreement,
 (a)
    
    Agreement means this OPCO Limited Partner Interest
Purchase Agreement;
 (b)
    
    Closing means the closing of the purchase and sale of the
Interests;
 (c)
    
    Common Units means common units, representing limited
partner interests, in Teekay Offshore;
 (d)
    
    Consideration means the Common Unit Portion, plus the
Cash Portion plus the GP Interest Portion of the consideration for the
Interests specified in Section 2.2;
 (e)
    
    Current Assets means the current assets of OPCO and its
Subsidiaries, as determined in accordance with GAAP and, to the extent
consistent with GAAP, OPCOs (and its Subsidiaries) past practices
consistently applied;
 (f)
    
    Current Liabilities means the current liabilities of
OPCO and its Subsidiaries, as determined in accordance with GAAP and, to the
extent consistent with GAAP, OPCOs (and its Subsidiaries) past practices
consistently applied;
 (g)
    
    Distribution means any cash distribution made by OPCO
pursuant to the Amended and Restated Agreement of Limited Partnership of
Teekay Offshore Operating L.P.;
 (h)
    
    Financial Statements means the consolidated statements of
income and balance sheet of OPCO for the fiscal year-ended and as at December
31, 2010;




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(i)
    
    GAAP means generally accepted accounting principles in
the United States, consistently applied over the periods in question;
 (j)
    
    General Partner Interest has the meaning set forth in the
First Amended and Restated Agreement of Limited Partnership of Teekay
Offshore;
 (k)
    
    General Partner Unit has the meaning set forth in the
First Amended and Restated Agreement of Limited Partnership of Teekay
Offshore;
 (l)
    
    Interests means the 49.0% limited partner interests of
Teekay Offshore Operating L.P. held by THL;
 (m)
    
    Liability means any indebtedness, liability or obligation
(whether known or unknown, whether asserted or unasserted, whether absolute
or contingent, whether accrued or unaccrued, whether liquidated or
unliquidated, whether incurred directly or consequentially, and whether due
or to become due), including any tax or other liability arising out of
applicable statutory, regulatory or common law, any contractual obligation
and any obligation arising out of tort;
 (n)
    
    Parties means THL and Teekay Offshore collectively, and
Party means either of them; and
 (o)
    
    Subsidiary has the meaning set forth in the First Amended
and Restated Agreement of Limited Partnership of Teekay Offshore.
 1.2
    
    Headings. Headings contained in this Agreement are included solely for convenience, are
not intended to be full or accurate descriptions of the content of any Section or Paragraph
and shall not be considered to be part of this Agreement.
 2.
    
    PURCHASE AND SALE OF INTERESTS
 2.1
    
    At Closing, THL shall sell and transfer to Teekay Offshore, and Teekay Offshore shall
purchase and receive from THL, the Interests.
 2.2
    
    In consideration for the Interests, Teekay Offshore shall (a) issue 7,562,814 Common
Units (the Common Unit Portion) to THL, (b) pay USD175,000,000 cash, as adjusted pursuant
to Section 2.5, (the Cash Portion) to THL and (c) issue General Partner Interests (the GP
Interest Portion) to Teekay Offshore GP L.L.C. equivalent to 2.0% of the Common Unit
Portion plus the issuance of the General Partner Interest (approximately $4,300,000 in
value, or 154,343 General Partner Units).
 2.3
    
    At Closing, Teekay Offshore shall pay THL the Consideration by (a) registering the Common
Unit Portion of the Consideration in the name of THL on Teekay Offshores books and records,
(b) wire transferring the Cash Portion of the Consideration in immediately available funds
to the account or accounts designated by THL and (c) recording the GP Interest Portion of
the Consideration for the benefit of Teekay Offshore GP L.L.C. on Teekay Offshores books
and records.
 2.4
    
    Promptly upon receipt of the Consideration, THL shall deliver to Teekay Offshore any
documents of title for the Interests evidencing ownership thereof in the name of Teekay
Offshore, and otherwise do all things necessary to have the Interests
transferred to Teekay Offshore and reflected on the books and records of OPCO.
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2.5
    
    Purchase Price Adjustment.Teekay Offshore shall be entitled to an adjustment to the Cash
Portion to reflect any Distributions by OPCO between and including January 1, 2011 and
Closing (the Pre-Closing Distributions). On or before ten (10) calendar days after
Closing, Teekay Offshore shall deliver to THL a statement showing all Pre-Closing
Distributions, along with a written request to reduce the Cash Portion by 49.0% of the
aggregate sum of Pre-Closing Distributions (the Adjustment Amount). THL shall promptly pay
the Adjustment Amount to Teekay Offshore by wire transfer of immediately available funds
within five (5) calendar days after receiving such request.
 3.
    
    CLOSING
 3.1
    
    The Closing of the transactions contemplated by this Agreement shall be held at the
offices of Teekay Offshore and shall occur substantially concurrent with the execution of
this Agreement.
 4.
    
    WARRANTIES OF THL
 4.1
    
    THL makes the following warranties to Teekay Offshore, and acknowledges that Teekay
Offshore is relying on these warranties in entering into this Agreement:
 (a)
    
    Organization and Good Standing.THL is a corporation duly
incorporated, organized and validly existing in good standing under the laws
of Bermuda.
 (b)
    
    Due Authorization, etc.THL has all necessary corporate
power, authority and capacity to enter into this Agreement and to perform its
obligations hereunder; and the execution and delivery of this Agreement have
been duly authorized by all necessary corporate action on the part of THL.
 (c)
    
    No Consents. No consent, approval or authorization of any
third party is required for consummation by THL of the transactions
contemplated by this Agreement, and the execution and delivery of this
Agreement and the performance of the transactions contemplated hereby do not
violate, conflict with, or cause a default under any contract, agreement,
document, or instrument, any law, rule, regulation or any judicial or
administrative decision to which THL or the Interests may be subject, or that
would create a lien, security interest, encumbrance or restriction of any
kind upon the Interests.
 (d)
    
    Title to Interests. THL is, and Teekay Offshore shall
become, on receipt of the Interests and payment therefor, the owner of the
Interests, with good and marketable title to the Interests, free and clear of
any title defects, mortgages, pledges, hypothecs, security interests, deemed
trusts, liens, charges, encumbrances or rights or claims of others of any
kind whatsoever.
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(e)
    
    Securities Representations. THL is acquiring the Common
Unit Portion of the Consideration solely for the account of THL and not with
a view to, or for resale in connection with, a distribution of all or any
part of the Common Units. THL acknowledges and understands that the Common
Units have not been registered with the U.S. Securities and Exchange
Commission or any non-U.S. securities commission or agency, and therefore
are subject to resale restrictions. THL agrees to the placement of a
legend on any Common Unit certificate or on the records of the transfer
agent to the effect that the Common Units may not be sold without
registration with the U.S. Securities and Exchange Commission or an
exemption from registration.
 (f)
    
    Financial Statements. Schedule 4.1 sets forth true,
complete and correct copies of the Financial Statements. Except as set forth
in Schedule 4.1, the Financial Statements: (i) were prepared in accordance
with GAAP, consistently applied throughout the periods presented, and (ii)
were prepared in accordance with, and are consistent with, the books and
records of OPCO and its Subsidiaries. The Financial Statements fairly present
in all material respects the assets, liabilities and financial condition of
OPCO and its Subsidiaries and the results of operations as at and for the
periods presented therein.
 (g)
    
    Absence of Undisclosed Liabilities. Neither OPCO nor any
Subsidiary has any Liabilities except (a) Liabilities set forth in OPCOs
consolidated balance sheet as of December 31, 2010 included in the Financial
Statements (the Latest Balance Sheet) or disclosed in the notes to the
Latest Balance Sheet, (b) Liabilities that have arisen after the Latest
Balance Sheet in the ordinary course of business and that are Current
Liabilities in amounts consistent with those reflected in the Latest Balance
Sheet (and are not Liabilities for breach of contract, breach of warranty,
product liability, tort or infringement, or a claim or lawsuit, or an
environmental liability), and (c) Liabilities expressly disclosed in the
Schedules attached to this Agreement.
 5.
    
    WARRANTIES OF TEEKAY OFFSHORE
 5.1
    
    Teekay Offshore makes the following warranties to THL, and acknowledges that THL is
relying on these warranties in entering into this Agreement:
 (a)
    
    Organization and Good Standing.Teekay Offshore is a
partnership duly formed, organized and validly existing in good standing
under the laws of the Marshall Islands.
 (b)
    
    Due Authorization, etc.Teekay Offshore has all necessary
power, authority and capacity to enter into this Agreement and to perform its
obligations hereunder; and the execution and delivery of this Agreement have
been duly authorized by all necessary action on the part of Teekay Offshore.
 (c)
    
    No Consents. No consent, approval or authorization of any
third party is required for consummation by Teekay Offshore of the
transactions contemplated by this Agreement, and the execution and delivery
of this Agreement and the performance of the transactions contemplated hereby
do not violate, conflict with, or cause a default under any contract,
agreement, document, or instrument, any law, rule, regulation or any
judicial or administrative decision to which Teekay Offshore may be
subject.
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(d)
    
    Title to Common Units and GP Interest. Upon the Closing
and payment of the Consideration in accordance with the terms of this
Agreement, good and marketable title to all of the Common Unit Portion of the
Consideration, free and clear of all mortgages, liens, security interests,
pledges, charges, encumbrances or claims of any kind will be sold to and vest
in THL, and the Common Units included in the Common Unit Portion of the
Consideration will be duly authorized and validly issued, fully paid and
nonassessable, and will not have been issued in violation of any preemptive
or similar rights. Upon the Closing and payment of the Consideration in
accordance with the terms of this Agreement, the GP Interest Portion of the
Consideration will vest in Teekay Offshore GP L.L.C., free and clear of all
mortgages, liens, security interests, pledges, charges, encumbrances or
claims of any kind (other than as set forth in the First Amended and Restated
Agreement of Limited Partnership of Teekay Offshore, as amended).
 6.
    
    NO COMMISSION; SURVIVAL; INDEMNIFICATION
 6.1
    
    Each Party warrants to the other Party that no individual, partnership, or corporation is
entitled to a brokerage commission, finders fee or other like payment in connection with
the purchase and sale of the Interests.
 6.2
    
    All representations and warranties made herein shall survive the Closing without
expiration; provided, however, that THLs representations and warranties set forth in
Sections 4.1(f) (Financial Statements) and 4.1(g) (Absence of Undisclosed Liabilities) will
survive until, and terminate on, March 8, 2014.
 6.3
    
    Teekay Offshore agrees to indemnify and hold THL harmless from any and all losses,
damages, claims, actions and proceedings, including any legal or other expenses, arising out
of any breach of any representation or warranty made by Teekay Offshore herein.
 6.4
    
    THL agrees to indemnify and hold Teekay Offshore harmless from any and all losses,
damages, claims, actions and proceedings, including any legal or other expenses, arising out
of any breach of any representation or warranty made by THL herein.
 7.
    
    NOTICES
 7.1
    
    Any notice, direction or other instrument required or permitted to be given by either
Party under this Agreement shall be in writing and shall be sufficiently given if delivered
personally, sent by prepaid first class mail or transmitted by facsimile or other form of
electronic communication during the transmission of which no indication of failure of
receipt is communicated to the sender:
 (a)
    
    in the case of a notice to Teekay Holdings Limited at:
 
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(b)
    
    in the case of a notice to Teekay Offshore Partners L.P.
at:
 
 8.
    
    GENERAL
 8.1
    
    Expenses. Except as otherwise agreed in writing by the Parties, costs and expenses
(including, without limitation, the fees and disbursements of legal counsel) incurred in
connection with this Agreement and the transaction contemplated under this Agreement shall
be paid by the Party incurring such expenses.
 8.2
    
    Assignment/Successors and Assigns. Neither this Agreement nor any rights or obligations
under this Agreement shall be assignable by either Party without the prior written consent
of the other Party, which shall not be unreasonably withheld or delayed. Subject to that
condition, this Agreement shall enure to the benefit of and be binding upon the Parties and
their respective heirs, executors, administrators, successors (including any successor by
reason of amalgamation of any Party) and permitted assigns.
 8.3
    
    Governing Law. This Agreement shall be governed by and construed under the laws of the
state of New York.
 8.4
    
    Further Assurances. Each Party agrees that upon the written request of any other Party,
it will do all such acts and execute all such further documents, conveyances, deeds,
assignments, transfers and the like, and will cause the doing of all such acts and will
cause the execution of all such further documents as are within its power to cause the doing
or execution of, as the other Party may from time to time reasonably request be done and
executed as may be required to consummate the transactions contemplated under this
Agreement, or as may be necessary or desirable to effect the purpose of this Agreement or
any document, agreement or instrument delivered under this Agreement and to carry out their
provisions or to better or more properly or fully evidence or give effect to the
transactions contemplated under this Agreement.
 8.5
    
    Public Notices. All notices to third parties and all other publicity concerning the
transactions contemplated by this Agreement shall be jointly planned and coordinated by THL
and Teekay Offshore and no Party shall act unilaterally in this regard without the prior
approval of the other Party (such approval not to be unreasonably delayed or withheld),
except where required to do so by law or by the applicable regulations or policies of any
regulatory agency of competent jurisdiction or any stock exchange.
 8.6
    
    Counterparts.This Agreement may be executed by the Parties in separate counterparts
each of which when so executed and delivered shall be an original, and all such counterparts
shall together constitute one and the same instrument.
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Teekay Holdings LimitedBy:
    
    /s/ Roy SpiresName: Roy SpiresTitle: PresidentTeekay Offshore Partners L.P.By: Teekay Offshore GP L.L.C., its general partnerBy:
    
    /s/ Peter EvensenName: Peter EvensenTitle: Chief Executive Officer