Document:

Exhibit
10.14

 

SARATOGA
INVESTMENT CORP.

First SUPPLEMENTAL NOTES PURCHASE AGREEMENT

 

Dated
as of January 28, 2021

 

To
the Purchaser Listed in the signature page: 

 

Ladies
and Gentlemen:

 

Reference
is made to that certain Note Purchase Agreement dated July 9, 2020 (the “Purchase Agreement”), by and between Saratoga
Investment Corp., a Maryland corporation (the “Corporation”) and The HCM Master Fund Limited (the “Purchaser”).
Each capitalized term used herein but not defined shall have the meaning ascribed to such term in the Purchase Agreement.

 

WHEREAS,
Section 1.1 of the Purchase Agreement provides that upon the mutual agreement of the Corporation and the Purchaser, the Corporation may
authorize Additional Notes or New Notes for sale to the Purchaser in a subsequent offering, in the aggregate, up to a maximum of $50,000,000;
and

 

WHEREAS,
the Company and the Purchaser desire to enter into this First Supplemental Notes Purchase Agreement (the “Agreement”)
in connection with issuance and sale of $10,000,000 aggregate principal amount of its 6.25% Notes due 2027 (the “2027 Notes”)
in a private offering, pursuant to an offering memorandum dated on or about the date hereof (the “Offering Memorandum”).

 

NOW
THEREFORE, in consideration of the mutual promises contained in this Agreement and other good and valuable consideration, the receipt
and sufficiency of which are hereby acknowledged, the parties to this Agreement, intending to be legally bound, hereby update the following
provisions of the Purchase Agreement and agree as follows:

 

		(1)	Section
                                            1.2 of the Purchase Agreement is replaced in its entirety for purposes of this Agreement
                                            with the following:

 

“Sale
and Purchase of the Notes. Subject to the terms and conditions herein provided, the Corporation hereby agrees to sell to the purchaser
listed in the signature page attached hereto (the “Purchaser”), and the Purchaser agrees to purchase from the Corporation,
at the Closing provided for in Section 2 hereof, that aggregate principal amount of the 2027 Notes specified directly opposite
its name in the signature page, at the purchase price of 97.25% of the principal amount thereof (the “Purchase Price”).
The Purchaser understands and acknowledges that it has made its own review of the investment merits and risks of the 2027 Notes.”

 

		(2)	The
                                            reference to “fifth supplement indenture” in Section 1.3 of the Purchase Agreement
                                            shall be replaced with “seventh supplemental indenture” for purposes of this
                                            Agreement.

 

		(3)	Section
                                            2.1 is hereby revised to reflect 11:00 A.M., New York time, on January 28, 2021 as the Closing
                                            Date for purposes of this Agreement.

 

     

     

    

 

		(4)	Section
                                            3.1(d) is hereby replaced in its entirety for purposes of this Agreement with the following:

 

The
Corporation shall have delivered to counsel for Purchaser an amount equal to the legal fees, subject to a cap of $10,000, incurred in
connection with the issuance of the 2027 Notes by wire transfer of immediately available funds pursuant to the wire instructions provided
by the counsel to the Purchaser.

 

		(5)	The
                                            reference to “Second Amended and Restated Bylaws” in Section 4.1(g) of the Purchase
                                            Agreement shall be replaced with “Third Amended and Restated Bylaws”.

 

Except
as set forth above, no other changes to the terms of the Purchase Agreement are intended by the parties thereto, are made, or shall be
deemed to be made, pursuant to this Agreement, and all provisions of the Purchase Agreement, including all exhibits thereto, unaffected
by this Agreement shall remain in full force and effect.

 

For
the avoidance of any doubt, the Purchase Agreement shall not be deemed to be amended (other than with respect to clause (5) above) and
remains unchanged with respect to the Notes issued thereunder.

 

 

 

 

 

 

 

[SIGNATURE
PAGE FOLLOWS]

 

    -2-

     

    

 

If
the foregoing correctly sets forth the agreement between the Corporation and the Purchaser, please indicate your acceptance in the space
provided for that purpose below.

 

	 	Very
                                            truly yours,

	 	 	 
	 	SARATOGA
    INVESTMENT CORP.
	 	 	 
	 	By:	/s/
    Henri J. Steenkamp
	 	Name: 	Henri
    J. Steenkamp
	 	Title:	Chief
    Financial Officer, 

Chief Compliance Office, 

Treasurer and Secretary

 

     

     

    

 

SIGNATURE
PAGE

 

This
Agreement is hereby accepted and agreed to as of the date hereof.

 

	 	 	 	Aggregate
    Amount of Principal to be Purchased:
	 	 	 	$10,000,000
	 	 	 	Purchase
    Price:
	 	 	 	$9,725,000
	 	 	 	 
	By:	/s/
    Erik Herzfeld	 	Date:
    January 28, 2021
	Name: 	Erik
    Herzfeld	 	 
	Title:	Authorized
    SignatoryExhibit 10.15

 

SARATOGA INVESTMENT
CORP.

Second SUPPLEMENTAL NOTES PURCHASE AGREEMENT

 

Dated as of September 8, 2022

 

To the Purchaser Listed in the signature page:

 

Ladies and Gentlemen:

 

Reference is made to that
certain Note Purchase Agreement dated July 9, 2020 (the “Purchase Agreement”), by and between Saratoga Investment Corp.,
a Maryland corporation (the “Corporation”) and The HCM Master Fund Limited (the “Purchaser”). Each
capitalized term used herein but not defined shall have the meaning ascribed to such term in the Purchase Agreement.

 

WHEREAS, Section 1.1 of the
Purchase Agreement provides that upon the mutual agreement of the Corporation and the Purchaser, the Corporation may authorize Additional
Notes or New Notes for sale to the Purchaser in a subsequent offering, in the aggregate, up to a maximum of $50,000,000; and

 

WHEREAS, the Corporation and
the Purchaser desire to enter into this Second Supplemental Notes Purchase Agreement (the “Agreement”) pursuant to
which (i) $12,000,000 in aggregate principal amount of the Company’s 7.00% Notes due 2025 (the “2025 Notes”)
will be sold and issued, and (ii) upon mutual agreement of the Corporation and the Purchaser, the Purchaser may purchase from the Corporation
up to an additional $8,000,000 aggregate principal of the 2025 Notes by September 30, 2022 (the “Additional 2025 Notes”),
each in a private offering, pursuant to an offering memorandum dated on or about the date hereof (the “Offering Memorandum”).

 

NOW THEREFORE, in consideration
of the mutual promises contained in this Agreement and other good and valuable consideration, the receipt and sufficiency of which are
hereby acknowledged, the parties to this Agreement, intending to be legally bound, hereby update the following provisions of the Purchase
Agreement and agree as follows:

 

		(1)	Section 1.2 of the Purchase Agreement is replaced in its entirety for purposes of this Agreement with
the following:

 

“Sale and Purchase
of the Notes. Subject to the terms and conditions herein provided, the Corporation hereby agrees to sell to the purchaser listed in
the signature page attached hereto (the “Purchaser”), and the Purchaser agrees to purchase from the Corporation, at
the Closing provided for in Section 2 hereof, that aggregate principal amount of the 2025 Notes specified directly opposite its
name in the signature page, at the purchase price of 97.000% of the principal amount thereof (the “Purchase Price”).
The Purchaser understands and acknowledges that it has made its own review of the investment merits and risks of the 2025 Notes.”

 

     

     

    

 

		(2)	The reference to “fifth supplement indenture” in Section 1.3 of the Purchase Agreement shall
be replaced with “eleventh supplemental indenture” for purposes of this Agreement.

 

		(3)	Section 2.1 is hereby revised to reflect 11:00 A.M., New York time, on September 8, 2022 as the Closing
Date for purposes of this Agreement.

 

		(4)	Section 3.1(d) is hereby replaced in its entirety for purposes of this Agreement with the following:

 

The Corporation shall have delivered
to counsel for Purchaser an amount equal to the legal fees, subject to a cap of $10,000, incurred in connection with the issuance of the
2025 Notes and any Additional 2025 Notes by wire transfer of immediately available funds pursuant to the wire instructions provided by
the counsel to the Purchaser.

 

		(5)	The reference to “Second Amended and Restated Bylaws” in Section 4.1(g) of the Purchase Agreement
shall be replaced with “Third Amended and Restated Bylaws”.

 

Except as set forth above,
no other changes to the terms of the Purchase Agreement are intended by the parties thereto, are made, or shall be deemed to be made,
pursuant to this Agreement, and all provisions of the Purchase Agreement, including all exhibits thereto, unaffected by this Agreement
shall remain in full force and effect.

 

For the avoidance of any
doubt, the Purchase Agreement shall not be deemed to be amended (other than with respect to clause (5) above) and remains unchanged with
respect to the Notes issued thereunder.

 

 

 

 

[SIGNATURE PAGE
FOLLOWS]

 

    -2-

     

    

 

If the foregoing correctly sets forth the agreement
between the Corporation and the Purchaser, please indicate your acceptance in the space provided for that purpose below.

 

	 	Very truly yours,
	 	 
	 	SARATOGA INVESTMENT CORP.
	 	 
	 	By: 	/s/ Henri J. Steenkamp
	 	Name: 	Henri J. Steenkamp
	 	Title: 	Chief Financial Officer,

 Chief Compliance Office, 

Treasurer and Secretary

 

     

     

    

 

SIGNATURE PAGE

 

This
Agreement is hereby accepted and agreed to as of the date hereof. 

 

	 	 	Aggregate Amount of Principal to be Purchased: 
	 	 	$12,000,000
	 	 	Purchase Price: 
	 	 	$11,640,000
	 	 	 
	By:	/s/ Erik Herzfeld	 	Date: September 8, 2022
	Name: 	 Erik Herzfeld	 	 
	Title:	Authorized Signatory

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00349-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00349-of-00352.parquet"}]]