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Form 8-K

sec.gov

8-K — SARATOGA INVESTMENT CORP.

Accession: 0001213900-26-093812

Filed: 2026-08-26

Period: 2026-08-26

CIK: 0001377936

Item: Entry into a Material Definitive Agreement

Item: Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

Item: Financial Statements and Exhibits

Documents

8-K — ea0303350-8k_saratoga.htm (Primary)

EX-4.2 — EIGHTEENTH SUPPLEMENTAL INDENTURE, DATED AS OF AUGUST 26, 2026, BY AND BETWEEN SARATOGA INVESTMENT CORP. AND U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (AS SUCCESSOR IN INTEREST TO U.S. BANK NATIONAL ASSOCIATION), AS TRUSTEE (ea030335001ex4-2.htm)

EX-5.1 — OPINION OF EVERSHEDS SUTHERLAND (US) LLP (ea030335001ex5-1.htm)

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8-K — CURRENT REPORT

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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, DC 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d)

of the Securities Exchange Act of 1934

Date of report (Date of earliest event reported):

August 26, 2026

SARATOGA INVESTMENT CORP.

(Exact Name of Registrant as Specified in Charter)

Maryland

814-00732

20-8700615

(State or Other Jurisdiction

of Incorporation)

(Commission File Number)

(IRS Employer

Identification No.)

535 Madison Avenue

New York, New York

10022

(Address of Principal Executive Offices)

(Zip Code)

Registrant’s telephone number, including

area code (212) 906-7800

Not Applicable

(Former Name or Former Address, if Changed Since

Last Report)

Check the appropriate box below if the Form 8-K filing is intended

to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction

A.2. below):

☐

Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐

Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐

Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐

Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class

Trading symbol(s)

Name of each exchange on which registered

Common Stock, par value $0.001 per share

SAR

New York Stock Exchange

6.00% Notes due 2027

SAT

New York Stock Exchange

8.00% Notes due 2027

SAJ

New York Stock Exchange

8.125% Notes due 2027

SAY

New York Stock Exchange

8.50% Notes due 2028

SAZ

New York Stock Exchange

7.50% Notes due 2031

SAV

New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth

company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange

Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant

has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant

to Section 13(a) of the Exchange Act.  ☐

Item 1.01. Entry into a Material Definitive Agreement.

In connection with the previously

announced public offering, on August 26, 2026, Saratoga Investment Corp. (the “Company”) and U.S. Bank Trust Company, National

Association, as trustee (as successor in interest to U.S. Bank National Association) (the “Trustee”), entered into an Eighteenth

Supplemental Indenture (the “Eighteenth Supplemental Indenture”) to the Base Indenture, dated May 10, 2013, by and between

the Company and the Trustee (the “Base Indenture”; and together with the Eighteenth Supplemental Indenture, the “Indenture”).

The Eighteenth Supplemental Indenture relates to the Company’s issuance and sale of $85.0 million in aggregate principal amount

of the Company’s 8.00% Notes due 2031 (the “Notes” and the issuance and sale of the Notes, the “Offering”).

The Notes bear interest at

a rate of 8.00% per year, payable quarterly on February 28, May 31, August 31, and November 30 of each year, beginning November 30,

2026. The Notes will mature on August 31, 2031 and

may be redeemed at the Company’s option, in whole or in part at any time, or from time to time on or after August 26, 2028,

at the redemption price of par, plus accrued and unpaid interest.

The

Company intends to use the net proceeds from the Offering and available cash to redeem in full the Company’s outstanding 6.00% notes

due 2027.

The Notes are the direct unsecured

obligations of the Company and rank pari passu with all existing and future unsecured,

unsubordinated indebtedness issued by the Company, senior to any of the Company’s future indebtedness that expressly

provides it is subordinated to the Notes, effectively subordinated to all of the existing and future secured indebtedness issued by the

Company (including indebtedness that is initially unsecured in respect of which the Company subsequently grants security), to the

extent of the value of the assets securing such indebtedness, and structurally subordinated to all existing and future indebtedness and

other obligations of any of the Company’s subsidiaries, including, without limitation, our special purpose vehicle financing credit

facility with Live Oak Banking Company, our special purpose vehicle financing credit facility with Valley National Bank, and the debentures

guaranteed by the U.S. Small Business Administration.

The Indenture contains certain

covenants, including certain covenants requiring the Company to comply with Section 18(a)(1)(A) as modified by Section 61(a)(2) of the

Investment Company Act of 1940, as amended (the “1940 Act”), or any successor provisions, whether or not the Company continues

to be subject to such provisions of the 1940 Act, but giving effect, in either case, to any exemptive relief granted to the Company by

the U.S. Securities and Exchange Commission (the “SEC”), to comply with Section 18(a)(1)(B) as modified by Section 61(a)(2)

of the 1940 Act, or any successor provisions, after giving effect to any exemptive relief granted to the Company by the SEC and subject

to certain other exceptions, and to provide financial information to the holders of the Notes and the Trustee if the Company is no longer

subject to the reporting requirements under the Securities Exchange Act of 1934, as amended. These covenants are subject to important

limitations and exceptions that are described in the Indenture.

The Offering was made pursuant

to the Company’s effective shelf registration statement on Form N-2 (File No. 333-292765) previously filed with the SEC, as

supplemented by a preliminary prospectus supplement dated August 18, 2026, the pricing term sheet filed with the SEC on August 18, 2026,

and a final prospectus supplement dated August 18, 2026. The transaction closed on August 26, 2026. The net proceeds to the Company were

approximately $82,043,750, based on a public offering price of 100% of par, after deducting the underwriting discount of $2,656,250 and

the estimated offering expenses of approximately $300,000 payable by the Company.

The foregoing descriptions

of the Eighteenth Supplemental Indenture and the Notes do not purport to be complete and are qualified in their entirety by reference

to the full text of the Eighteenth Supplemental Indenture and the form of global note representing the Notes, respectively, which is filed

as Exhibits 4.2 and 4.3 hereto, respectively, and incorporated by reference herein.

1

Item 2.03. Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant.

The information required

by Item 2.03 contained in Item 1.01 of this Current Report on Form 8-K is incorporated herein by reference.

Item 9.01. Financial Statements and Exhibits.

(d) Exhibits

Exhibit No.

Description

4.1

Form of Indenture by and between Saratoga Investment Corp. and U.S. Bank National Association, as trustee (Incorporated by reference to Exhibit (d)(4) to Pre-Effective Amendment No. 2 to the Registration Statement on Form N-2 (File No. 333-186323) filed on April 30, 2013).

4.2

Eighteenth Supplemental Indenture, dated as of August 26, 2026, by and between Saratoga Investment Corp. and U.S. Bank Trust Company, National Association (as successor in interest to U.S. Bank National Association), as trustee.

4.3

Form of Global Note with respect to the 8.00% Notes due 2031 (Incorporated by reference to Exhibit 4.2 hereto).

5.1

Opinion of Eversheds Sutherland (US) LLP.

23.1

Consent of Eversheds Sutherland (US) LLP (included in Exhibit 5.1 hereto).

104

Cover Page Interactive Data File (embedded within the Inline XBRL document)

2

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934,

the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

SARATOGA INVESTMENT CORP.

Date: August 26, 2026

By:

/s/ Henri J. Steenkamp

Name:

Henri J. Steenkamp

Title:

Chief Financial Officer, Chief Compliance Officer, Treasurer and Secretary

3

EX-4.2 — EIGHTEENTH SUPPLEMENTAL INDENTURE, DATED AS OF AUGUST 26, 2026, BY AND BETWEEN SARATOGA INVESTMENT CORP. AND U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (AS SUCCESSOR IN INTEREST TO U.S. BANK NATIONAL ASSOCIATION), AS TRUSTEE

EX-4.2

Filename: ea030335001ex4-2.htm · Sequence: 2

Exhibit 4.2

EIGHTEENTH SUPPLEMENTAL INDENTURE

between

SARATOGA INVESTMENT CORP.

and

U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION,

as Trustee

Dated as of August 26, 2026

THIS EIGHTEENTH SUPPLEMENTAL

INDENTURE (this “Eighteenth Supplemental Indenture”), dated as of August 26, 2026, is between Saratoga Investment Corp., a

Maryland corporation (the “Company”), and U.S. Bank Trust Company, National Association (as successor in interest to U.S.

Bank National Association), as trustee (the “Trustee”). All capitalized terms used herein shall have the meaning set forth

in the Base Indenture (as defined below).

RECITALS OF THE COMPANY

The Company and the Trustee

executed and delivered an Indenture, dated as of May 10, 2013 (the “Base Indenture” and, as supplemented by this Eighteenth

Supplemental Indenture, the “Indenture”), to provide for the issuance by the Company from time to time of the Company’s

unsecured debentures, notes or other evidences of indebtedness (the “Securities”), to be issued in one or more series as provided

in the Indenture.

The Company desires to issue

and sell $85,000,000 aggregate principal amount (or up to $97,750,000 aggregate principal amount if the underwriters’ option to

purchase additional Securities is exercised in full) of the Company’s 8.00% Notes due 2031 (the “Notes”).

The Company previously entered

into the First Supplemental Indenture, dated as of May 10, 2013 (the “First Supplemental Indenture”), the Second Supplemental

Indenture, dated as of December 21, 2016 (the “Second Supplemental Indenture”), the Third Supplemental Indenture, dated as

of August 28, 2018 (the “Third Supplemental Indenture”), the Fourth Supplemental Indenture,

dated as of June 24, 2020 (the “Fourth Supplemental Indenture”), the Fifth Supplemental Indenture, dated as of July 9, 2020

(the “Fifth Supplemental Indenture”), the Sixth Supplemental Indenture, dated as of December 29, 2020 (the “Sixth Supplemental

Indenture”), and the Seventh Supplemental Indenture, dated as of January 28, 2021 (the “Seventh Supplemental Indenture”),

the Eighth Supplemental Indenture, dated as of March 10, 2021 (the “Eighth Supplemental Indenture”), the Ninth Supplemental

Indenture, dated as of January 19, 2022 (the “Ninth Supplemental Indenture”), the Tenth Supplemental Indenture, dated

as of April 27, 2022 (the “Tenth Supplemental Indenture”), the Eleventh Supplemental Indenture, dated as of September 8, 2022

(the “Eleventh Supplemental Indenture”), the Twelfth Supplemental Indenture, dated as of October 27, 2022 (the “Twelfth

Supplemental Indenture”), the Thirteenth Supplemental Indenture, dated as of December 13, 2022 (the “Thirteenth Supplemental

Indenture”), the Fourteenth Supplemental Indenture, dated as of March 31, 2023 (the Fourteenth Supplemental Indenture”), the

Fifteenth Supplemental Indenture, dated as of April 14, 2023 (the “Fifteenth Supplemental Indenture”), the Sixteenth Supplemental

Indenture, dated as of February 6, 2026 (the “Sixteenth Supplemental Indenture”), and the Seventeenth Supplemental Indenture,

dated as of April 10, 2026 (the “Seventeenth Supplemental Indenture”), each of which amended and supplemented the Base Indenture.

Neither the First Supplemental Indenture, the Second Supplemental Indenture, the Third Supplemental

Indenture, the Fourth Supplemental Indenture, the Fifth Supplemental Indenture, the Sixth Supplemental Indenture, the Seventh Supplemental

Indenture, the Eighth Supplemental Indenture, the Ninth Supplemental Indenture, the Tenth Supplemental Indenture, the Eleventh

Supplemental Indenture, the Twelfth Supplemental Indenture, the Thirteenth Supplemental Indenture, the Fourteenth Supplemental Indenture,

the Fifteenth Supplemental Indenture, the Sixteenth Supplemental Indenture, nor the Seventeenth Supplemental Indenture is applicable to

the Notes.

Sections 901(4) and 901(6)

of the Base Indenture provide that without the consent of Holders of the Securities of any series issued under the Indenture, the Company,

when authorized by or pursuant to a Board Resolution, and the Trustee, at any time and from time to time, may enter into one or more indentures

supplemental to the Base Indenture in form reasonably satisfactory to the Trustee to (i)

change or eliminate any of the provisions of the Indenture when there is no Security Outstanding of any series created prior to the execution

of the supplemental indenture that is entitled to the benefit of such provision and (ii) establish the form or terms of Securities of

any series as permitted by Section 201 and Section 301 of the Base Indenture.

2

The Company desires to establish

the form and terms of the Notes and to modify, alter, supplement and change certain provisions of the Base Indenture for the benefit of

the Holders of the Notes (except as may be provided in a future supplemental indenture to the Indenture (each, a “Future Supplemental

Indenture”)).

The Company has duly authorized

the execution and delivery of this Eighteenth Supplemental Indenture to provide for the issuance of the Notes and all acts and things

necessary to make this Eighteenth Supplemental Indenture a valid, binding, and legal obligation of the Company and to constitute a valid

agreement of the Company, in accordance with its terms, have been done and performed.

NOW, THEREFORE, for and in

consideration of the premises and the purchase of the Notes by the Holders thereof, it is mutually agreed, for the equal and proportionate

benefit of all Holders of the Notes, as follows:

ARTICLE

I

TERMS OF THE NOTES

Section 1.01 Terms

of the Notes. The following terms relating to the Notes are hereby established:

(a) The

Notes shall constitute a series of Senior Securities having the title “8.00% Notes due 2031.” The Notes shall bear a CUSIP

number of 80349A 844 and an ISIN number of US80349A8449.

(b) The

aggregate principal amount of the Notes that may be initially authenticated and delivered under the Indenture (except for Notes authenticated

and delivered upon registration of, transfer of, or in exchange for, or in lieu of, other Notes pursuant to Sections 304, 305, 306, 906,

1107 or 1305 of the Base Indenture, and except for any Securities that, pursuant to Section 303 of the Base Indenture, are deemed never

to have been authenticated and delivered under the Indenture) shall be $85,000,000 (or up to $97,750,000 aggregate principal amount if

the underwriters’ option to purchase additional Securities is exercised in full). Under a Board Resolution, Officers’ Certificate

pursuant to Board Resolutions or an indenture supplement, the Company may from time to time, without the consent of the Holders of Notes,

issue additional Notes (in any such case “Additional Notes”) having the same ranking and the same interest rate, maturity

and other terms as the Notes; provided that, if such Additional Notes are not fungible with

the Notes (or any other tranche of Additional Notes) for U.S. federal income tax purposes, then such Additional Notes will have different

CUSIP and ISIN numbers from the Notes (and any such other tranche of Additional Notes). Any Additional Notes and the existing Notes

will constitute a single series under the Indenture and all references to the relevant Notes herein shall include the Additional Notes

unless the context otherwise requires.

(c) The

entire outstanding principal of the Notes shall be payable on August 31, 2031, unless earlier redeemed or repurchased in accordance with

the provisions of this Eighteenth Supplemental Indenture.

(d) The

rate at which the Notes shall bear interest shall be 8.00% per annum. The date from which interest shall accrue on the Notes shall be

August 26, 2026, or the most recent Interest Payment Date to which interest has been paid or provided for; the Interest Payment Dates

for the Notes shall be February 28, May 31, August 31 and November 30 of each year, commencing November 30, 2026 (if an Interest Payment

Date falls on a day that is not a Business Day, then the applicable interest payment will be made on the next succeeding Business Day

and no additional interest will accrue as a result of such delayed payment); the initial interest period will be the period from and including

August 26, 2026, to, but excluding, the initial Interest Payment Date, and the subsequent interest periods will be the periods from and

including an Interest Payment Date to, but excluding, the next Interest Payment Date or the Stated Maturity, as the case may be; the interest

so payable, and punctually paid or duly provided for, on any Interest Payment Date, will be paid to the Person in whose name the Note

(or one or more Predecessor Securities) is registered at the close of business on the Regular Record Date for such interest, which shall

be February 15, May 15, August 15 and November 15 (whether or not a Business Day), as the case may be, next preceding such Interest Payment

Date. Payment of principal of (and premium, if any, on) and any such interest on the Notes will be made at the office of the Trustee located

at 60 Livingston Avenue, St. Paul, MN 55107, Attention: Saratoga Investment Corp. (8.00% Notes Due 2031) or at such other address as designated

by the Trustee, in such coin or currency of the United States of America as at the time of payment is legal tender for payment of public

and private debts; provided, however, that at the option of the Company payment of interest may be made by check mailed to the

address of the Person entitled thereto as such address shall appear in the Security Register; provided, further, however, that

so long as the Notes are registered to Cede & Co., such payment will be made by wire transfer in accordance with the procedures established

by The Depository Trust Company and the Trustee. Interest on the Notes will be computed on the basis of a 360-day year of twelve 30-day

months.

3

(e) The

Notes shall be initially issuable in global form (each such Note, a “Global Note”). The Global Notes and the Trustee’s

certificate of authentication thereon shall be substantially in the form of Exhibit A to this Eighteenth Supplemental Indenture.

Each Global Note shall represent the aggregate amount of the outstanding Notes as shall be specified therein and each shall provide that

it shall represent the aggregate amount of outstanding Notes from time to time endorsed thereon and that the aggregate amount of outstanding

Notes represented thereby may from time to time be reduced or increased, as appropriate, to reflect exchanges and redemptions. Any endorsement

of a Global Note to reflect the amount of any increase or decrease in the amount of outstanding Notes represented thereby shall be made

by the Trustee or the Security Registrar, in accordance with Sections 203 and 305 of the Base Indenture.

(f) The

depositary for such Global Notes (the “Depositary”) shall be The Depository Trust Company, New York, New York. The Security

Registrar with respect to the Global Notes shall be the Trustee.

(g) The

Notes shall be defeasible pursuant to Section 1402 or Section 1403 of the Base Indenture. Covenant defeasance contained in Section 1403

of the Base Indenture shall apply to the covenants contained in Sections 1006, 1008 and 1009 of the Indenture.

(h) The

Notes shall be redeemable pursuant to Section 1101 of the Base Indenture and as follows:

(i) The

Notes will be redeemable in whole or in part at any time or from time to time, at the option of the Company, on or after August 26, 2028,

at a redemption price equal to 100% of the outstanding principal amount thereof, plus accrued and unpaid interest payments otherwise payable

for the then-current quarterly interest period accrued to, but excluding, the date fixed for redemption.

(ii) Notice

of redemption shall be given in writing and mailed, first-class postage prepaid or by overnight courier guaranteeing next-day delivery,

to each Holder of the Notes to be redeemed, not less than thirty (30) nor more than sixty (60) days prior to the Redemption Date, at the

Holder’s address appearing in the Security Register. All notices of redemption shall contain the information set forth in Section

1104 of the Base Indenture.

(iii) Any

exercise of the Company’s option to redeem the Notes will be done in compliance with the Indenture and the Investment Company Act,

to the extent applicable.

(iv) If

the Company elects to redeem only a portion of the Notes, the Trustee or, with respect to the Global

Notes, the Depositary will determine the method for selecting the particular Notes to be redeemed, in accordance with Section 1103

of the Base Indenture and the Investment Company Act and the rules of any national securities exchange or quotation system on which the

Notes are listed, in each case to the extent applicable.

(v) Unless

the Company defaults in payment of the Redemption Price, on and after the Redemption Date, interest will cease to accrue on the Notes

called for redemption hereunder.

(i) The

Notes shall not be subject to any sinking fund pursuant to Section 1201 of the Base Indenture.

(j) The

Notes shall be issuable in denominations of $25 and integral multiples of $25 in excess thereof.

(k) Holders

of the Notes will not have the option to have the Notes repaid prior to the Stated Maturity.

(l) The

Notes are hereby designated as “Senior Securities” under the Indenture.

4

ARTICLE

II

COVENANTS

Section 2.01 Except

as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under

the Indenture, whether now or hereafter issued and Outstanding, Article Ten of the Base Indenture shall be amended by adding the following

new Sections 1009, 1010 and 1011 thereto, each as set forth below:

“Section 1009. Section 18(a)(1)(A)

of the Investment Company Act.

The Company hereby

agrees that for the period of time during which the Notes are Outstanding, the Company will not violate (whether or not it is subject

to) Section 18(a)(1)(A) as modified by Section 61(a)(2) of the Investment Company Act as may be

applicable to the Company from time to time or any successor provisions thereto, whether or not the Company continues to be subject

to such provisions of the Investment Company Act, but giving effect to any exemptive relief granted to the Company by the Commission.”

“Section 1010. Section 18(a)(1)(B)

of the Investment Company Act.

The Company hereby agrees

that, for the period of time during which the Notes are Outstanding, the Company will not violate Section 18(a)(1)(B) as modified by Section

61(a)(2) of the Investment Company Act or any successor provisions thereto, whether or not the Company is subject to such provisions of

the Investment Company Act, and after giving effect to any exemptive relief granted to the Company by the Commission, except that the

Company may declare a cash dividend or distribution, notwithstanding the prohibition contained in Section 18(a)(1)(B) as modified by Section

61(a)(2) of the Investment Company Act or any successor provisions thereto, but only up to such amount as is necessary in order for the

Company to maintain its status as a regulated investment company under Subchapter M of the Code; provided, however, that the prohibition

in this Section 1010 shall not apply until such time as the Company’s asset coverage has been below the minimum asset coverage required

pursuant to Section 18(a)(1)(B) as modified by Section 61(a)(2) of the Investment Company Act or any successor provisions thereto (after

giving effect to any exemptive relief granted to the Company by the Commission) for more than six (6) consecutive months.”

“Section 1011. Commission Reports

and Reports to Holders.

If, at any time,

the Company is not subject to the reporting requirements of Sections 13 or 15(d) of the Exchange Act to file any periodic reports with

the Commission, the Company agrees to furnish to the Holders of the Notes and the Trustee for the period of time during which the Notes

are Outstanding: (i) within 90 days after the end of the each fiscal year of the Company (which fiscal year ends on February 28 (or February

29 during a leap year)), audited annual consolidated financial statements of the Company and (ii) within 45 days after the end of each

fiscal quarter of the Company (other than the Company’s fourth fiscal quarter), unaudited interim consolidated financial statements

of the Company. All such financial statements shall be prepared, in all material respects, in accordance with GAAP.”

ARTICLE

III

MEETINGS

OF HOLDERS OF SECURITIES

Section 3.01 Except

as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under

the Indenture, whether now or hereafter issued and Outstanding, Section 1505 of the Base Indenture shall be amended by replacing clause

(c) thereof with the following:

“(c) At any meeting

of Holders, each Holder of a Security of such series or proxy shall be entitled to one vote for each $25.00 principal amount of the Outstanding

Securities of such series held or represented by such Holder; provided, however, that no vote shall be cast or counted at

any meeting in respect of any Security challenged as not Outstanding and ruled by the chairman of the meeting to be not Outstanding. The

chairman of the meeting shall have no right to vote, except as a Holder of a Security of such series or proxy.”

5

ARTICLE

IV

MISCELLANEOUS

Section 4.01 This

Eighteenth Supplemental Indenture and the Notes shall be governed by and construed in accordance with the law of the State of New York,

without regard to principles of conflicts of laws. This Eighteenth Supplemental Indenture is subject to the provisions of the Trust Indenture

Act that are required to be part of the Indenture and shall, to the extent applicable, be governed by such provisions.

Section 4.02 In

case any provision in this Eighteenth Supplemental Indenture or in the Notes shall be invalid, illegal or unenforceable, the validity,

legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby.

Section 4.03 This

Eighteenth Supplemental Indenture may be executed in counterparts, each of which will be

an original, but such counterparts will together constitute but one and the same Eighteenth Supplemental

Indenture. The exchange of copies of this Eighteenth Supplemental Indenture and of signature

pages by facsimile, .pdf transmission, email or other electronic means shall constitute effective execution and delivery of this Eighteenth

Supplemental Indenture for all purposes. Signatures of the parties hereto transmitted by facsimile,

.pdf transmission, email or other electronic means shall be deemed to be their original signatures for all purposes. For the avoidance

of doubt, all notices, approvals, consents, requests and any communications hereunder or with respect to the Eighteenth Supplemental Indenture

must be in writing (provided that any communication sent to Trustee hereunder must be in the form of a document that is signed manually

or by way of a digital signature provided by DocuSign or Adobe (or such other digital signature provider as specified in writing to Trustee

by the authorized representative), in English. The Company agrees to assume all risks arising out of the use of using digital signatures

and electronic methods to submit communications to Trustee, including without limitation the risk of Trustee acting on unauthorized instructions,

and the risk of interception and misuse by third parties.

Section 4.04 The

Base Indenture, as supplemented and amended by this Eighteenth Supplemental Indenture, is in all respects ratified and confirmed, and

the Base Indenture and this Eighteenth Supplemental Indenture shall be read, taken and construed as one and the same instrument with respect

to the Notes. All provisions included in this Eighteenth Supplemental Indenture supersede any conflicting provisions included in the Base

Indenture with respect to the Notes, unless not permitted by law. The Trustee accepts the trusts created by the Base Indenture, as supplemented

by this Eighteenth Supplemental Indenture, and agrees to perform the same upon the terms and conditions of the Base Indenture, as supplemented

by this Eighteenth Supplemental Indenture.

Section 4.05 The

provisions of this Eighteenth Supplemental Indenture shall become effective as of the date hereof.

Section 4.06 Notwithstanding

anything else to the contrary herein, the terms and provisions of this Eighteenth Supplemental Indenture shall apply only to the Notes

and shall not apply to any other series of Securities under the Indenture and this Eighteenth Supplemental Indenture shall not and does

not otherwise affect, modify, alter, supplement or change the terms and provisions of any other series of Securities under the Indenture,

whether now or hereafter issued and Outstanding.

Section 4.07 The

recitals contained herein and in the Notes shall be taken as the statements of the Company, and the Trustee assumes no responsibility

for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Eighteenth Supplemental Indenture,

the Notes or any Additional Notes, except that the Trustee represents that it is duly authorized to execute and deliver this Eighteenth

Supplemental Indenture, authenticate the Notes and any Additional Notes and perform its obligations hereunder. The Trustee shall not be

accountable for the use or application by the Company of the Notes or any Additional Notes or the proceeds thereof. All

of the provisions contained in the Indenture in respect of the rights, privileges, immunities, powers, and duties of the Trustee shall

be applicable in respect of this Eighteenth Supplemental Indenture as fully and with like force and effect as though fully set forth in

full herein.

6

IN WITNESS WHEREOF, the parties

hereto have caused this Eighteenth Supplemental Indenture to be duly executed as of the date first above written.

SARATOGA INVESTMENT CORP.

By:

/s/ Henri J. Steenkamp

Name:

Henri J. Steenkamp

Title:

Chief Financial Officer, Chief Compliance Officer, Treasurer and Secretary

U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (as successor in interest to U.S. Bank National Association), as Trustee

By:

/s/ Adina M. Casper

Name:

Adina M. Casper

Title:

Vice President

[Signature page to Eighteenth Supplemental

Indenture]

7

Exhibit A – Form of Global Note

This Security is a Global Note within the

meaning of the Indenture hereinafter referred to and is registered in the name of The Depository Trust Company or a nominee thereof. This

Security may not be exchanged in whole or in part for a Security registered, and no transfer of this Security in whole or in part may

be registered, in the name of any Person other than The Depository Trust Company or a nominee thereof, except in the limited circumstances

described in the Indenture.

Unless this certificate is presented by an

authorized representative of The Depository Trust Company to the issuer or its agent for registration of transfer, exchange or payment

and such certificate issued in exchange for this certificate is registered in the name of Cede & Co., or such other name as requested

by an authorized representative of The Depository Trust Company, any transfer, pledge or other use hereof for value or otherwise by or

to any person is wrongful, as the registered owner hereof, Cede & Co., has an interest herein.

Saratoga Investment Corp.

No.

$

CUSIP No. 80349A 844

ISIN No. US80349A8449

8.00% Notes due 2031

Saratoga Investment Corp.,

a corporation duly organized and existing under the laws of Maryland (herein called the “Company”, which term includes any

successor Person under the Indenture hereinafter referred to), for value received, hereby promises to pay to Cede & Co., or registered

assigns, the principal sum of                     Dollars (U.S. $       ) on August 31, 2031 and to pay interest thereon from August 26, 2026 or from the most recent

Interest Payment Date to which interest has been paid or duly provided for, quarterly on February 28, May 31, August 31 and November 30

in each year, commencing November 30, 2026 at the rate of 8.00% per annum, until the principal hereof is paid or made available for payment.

The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided in such Indenture, be

paid to the Person in whose name this Security is registered at the close of business on the Regular Record Date for such interest, which

shall be February 15, May 15, August 15 and November 15 (whether or not a Business Day), as the case may be, next preceding such Interest

Payment Date. Any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular

Record Date and may either be paid to the Person in whose name this Security is registered at the close of business on a Special Record

Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice whereof shall be given to Holders of Securities of

this series not less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent

with the requirements of any securities exchange on which the Securities of this series may be listed, and upon such notice as may be

required by such exchange, all as more fully provided in said Indenture. This Security may be issued as part of a series.

Payment of the principal of

(and premium, if any, on) and any such interest on this Security will be made at the office of the Trustee located at 60 Livingston Avenue,

St. Paul, MN 55107, Attention: Saratoga Investment Corp. (8.00% Notes due 2031) or at such other address as designated by the Trustee,

in such coin or currency of the United States of America as at the time of payment is legal tender for payment of public and private debts;

provided, however, that at the option of the Company payment of interest may be made by check mailed to the address of the

Person entitled thereto as such address shall appear in the Security Register; provided, further, however, that so long as this

Security is registered to Cede & Co., such payment will be made by wire transfer in accordance with the procedures established by

The Depository Trust Company and the Trustee.

Reference is hereby made to

the further provisions of this Security set forth on the reverse hereof, which further provisions shall for all purposes have the same

effect as if set forth at this place.

Unless the certificate of

authentication hereon has been executed by the Trustee referred to on the reverse hereof by manual signature, this Security shall not

be entitled to any benefit under the Indenture or be valid or obligatory for any purpose.

8

IN WITNESS WHEREOF, the Company has caused

this instrument to be duly executed.

Dated:

SARATOGA INVESTMENT CORP.

By:

Name:

Title:

Attest

By:

Name:

Title:

[Global Note –

Eighteenth Supplemental Indenture]

9

This is one of the Securities of the series designated

therein referred to in the within-mentioned Indenture.

Dated:

U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION (as successor in interest to U.S. Bank National Association),

as Trustee

By:

Authorized Signatory

[Global Note –

Eighteenth Supplemental Indenture]

10

Saratoga Investment Corp.

8.00% Notes due 2031

This Security is one of a

duly authorized issue of Senior Securities of the Company (herein called the “Securities”), issued and to be issued in one

or more series under an Indenture, dated as of May 10, 2013 (herein called the “Base Indenture”, which term shall have the

meaning assigned to it in such instrument), between the Company and U.S. Bank Trust Company, National Association (as successor in interest

to U.S. Bank National Association), as Trustee (herein called the “Trustee”, which term includes any successor trustee under

the Base Indenture), and reference is hereby made to the Base Indenture for a statement of the respective rights, limitations of rights,

duties and immunities thereunder of the Company, the Trustee, and the Holders of the Securities and of the terms upon which the Securities

are, and are to be, authenticated and delivered, as supplemented by the Eighteenth Supplemental Indenture relating to the Securities,

dated as of August 26, 2026, by and between the Company and the Trustee (herein called the “Eighteenth Supplemental Indenture”;

the Eighteenth Supplemental Indenture and together with the Base Indenture, collectively are herein called the “Indenture”).

In the event of any conflict between the Base Indenture and the Eighteenth Supplemental Indenture, the Eighteenth Supplemental Indenture

shall govern and control.

This Security is one of the

series designated on the face hereof, which series is initially limited in aggregate principal amount to $   . Under a Board Resolution,

Officers’ Certificate pursuant to Board Resolutions or an indenture supplement, the Company may from time to time, without the consent

of the Holders of Securities, issue additional Securities of this series (in any such case “Additional Securities”) having

the same ranking and the same interest rate, maturity and other terms as the Securities; provided

that, if such Additional Securities are not fungible with the Securities (or any other tranche of Additional Securities for U.S. federal

income tax purposes), then such Additional Securities will have different CUSIP and ISIN numbers from the Securities (and any such other

tranche of Additional Securities). Any Additional Securities and the existing Securities will constitute a single series under

the Indenture and all references to the relevant Securities herein shall include the Additional Securities unless the context otherwise

requires. The aggregate amount of outstanding Securities represented hereby may from time to time be reduced or increased, as appropriate,

to reflect exchanges and redemptions.

The Securities of this series

are subject to redemption in whole or in part at any time or from time to time, at the option of the Company, on or after August 26, 2028,

at a redemption price per security equal to 100% of the outstanding principal amount thereof plus accrued and unpaid interest payments

otherwise payable for the then-current quarterly interest period accrued to, but excluding, the date fixed for redemption.

Notice of redemption shall

be given in writing and mailed, first-class postage prepaid or by overnight courier guaranteeing next-day delivery, to each Holder of

the Securities to be redeemed, not less than thirty (30) nor more than sixty (60) days prior to the Redemption Date, at the Holder’s

address appearing in the Security Register. All notices of redemption shall contain the information set forth in Section 1104 of the Base

Indenture.

Any exercise of the Company’s

option to redeem the Securities will be done in compliance with the Indenture and the Investment Company Act, to the extent applicable.

If the Company elects to redeem

only a portion of the Securities, the Trustee or, with respect to global Securities, the Depositary

will determine the method for selecting the particular Securities to be redeemed, in accordance with Section 1.01 of the Eighteenth

Supplemental Indenture and Section 1103 of the Base Indenture. In the event of redemption of this Security in part only, a new Security

or Securities of this series and of like tenor for the unredeemed portion hereof will be issued in the name of the Holder hereof upon

the cancellation hereof.

Unless the Company defaults

in payment of the Redemption Price, on and after the Redemption Date, interest will cease to accrue on the Securities called for redemption.

Holders of Securities do not

have the option to have the Securities repaid prior to August 31, 2031.

The Indenture contains provisions

for defeasance at any time of the entire indebtedness of this Security or certain restrictive covenants and Events of Default with respect

to this Security, in each case upon compliance with certain conditions set forth in the Indenture.

If an Event of Default with

respect to Securities of this series shall occur and be continuing, the principal of the Securities of this series may be declared due

and payable in the manner and with the effect provided in the Indenture.

11

The Indenture permits, with

certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Company and the

rights of the Holders of the Securities of each series to be affected under the Indenture at any time by the Company and the Trustee with

the consent of the Holders of not less than a majority in principal amount of the Securities at the time Outstanding of each series to

be affected. The Indenture also contains provisions permitting the Holders of specified percentages in principal amount of the Securities

of each series at the time Outstanding, on behalf of the Holders of all Securities of such series, to waive compliance by the Company

with certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such consent or waiver

by the Holder of this Security shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any

Security issued upon the registration of transfer hereof or in exchange herefor or in lieu hereof, whether or not notation of such consent

or waiver is made upon this Security.

As provided in and subject

to the provisions of the Indenture, the Holder of this Security shall not have the right to institute any proceeding with respect to the

Indenture or for the appointment of a receiver or trustee or for any other remedy thereunder, unless such Holder shall have previously

given the Trustee written notice of a continuing Event of Default with respect to the Securities of this series, the Holders of not less

than 25% in principal amount of the Securities of this series at the time Outstanding shall have made written request to the Trustee to

institute proceedings in respect of such Event of Default as Trustee and offered the Trustee indemnity, security, or both reasonably satisfactory

to the Trustee against the costs, expenses and liabilities to be incurred in compliance with such request, and the Trustee shall not have

received from the Holders of a majority in principal amount of Securities of this series at the time Outstanding a direction inconsistent

with such request, and shall have failed to institute any such proceeding, for sixty (60) days after receipt of such notice, request and

offer of indemnity and/or security. The foregoing shall not apply to any suit instituted by the Holder of this Security for the enforcement

of any payment of principal hereof or any premium or interest hereon on or after the respective due dates expressed herein.

No reference herein to the

Indenture and no provision of this Security or of the Indenture shall alter or impair the obligation of the Company, which is absolute

and unconditional, to pay the principal of and any premium and interest on this Security at the times, place and rate, and in the coin

or currency, herein prescribed.

As provided in the Indenture

and subject to certain limitations therein set forth, the transfer of this Security is registrable in the Security Register, upon surrender

of this Security for registration of transfer at the office or agency of the Company in any place where the principal of and any premium

and interest on this Security are payable, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to

the Company and the Security Registrar duly executed by, the Holder hereof or his attorney duly authorized in writing, and thereupon one

or more new Securities of this series and of like tenor, of authorized denominations and for the same aggregate principal amount, will

be issued to the designated transferee or transferees.

The Securities of this series

are issuable only in registered form without coupons in denominations of $25 and any integral multiples of $25 in excess thereof. As provided

in the Indenture and subject to certain limitations therein set forth, Securities of this series are exchangeable for a like aggregate

principal amount of Securities of this series and of like tenor of a different authorized denomination, as requested by the Holder surrendering

the same.

No service charge shall be

made for any such registration of transfer or exchange, but the Company, the Trustee, or the Security Registrar may require payment of

a sum sufficient to cover any tax or other governmental charge payable in connection therewith.

Prior to due presentment of

this Security for registration of transfer, the Company, the Trustee, or the Security Registrar and any agent of the Company, the Trustee,

or the Security Registrar may treat the Person in whose name this Security is registered as the owner hereof for all purposes, whether

or not this Security be overdue, and none of the Company, the Trustee, the Security Registrar or any agent thereof shall be affected by

notice to the contrary.

All terms used in this Security

which are defined in the Indenture shall have the meanings assigned to them in the Indenture.

The Indenture and this Security

shall be governed by and construed in accordance with the laws of the State of New York, without regard to principles of conflicts of

laws.

To the extent any provision

of this Security conflicts with the express provisions of the Indenture, the provisions of the Indenture shall govern and be controlling.

12

EX-5.1 — OPINION OF EVERSHEDS SUTHERLAND (US) LLP

EX-5.1

Filename: ea030335001ex5-1.htm · Sequence: 3

Exhibit 5.1

Eversheds Sutherland (US) LLP

700 Sixth Street, NW, Suite 700

Washington,

DC 20001-3980

August 26, 2026

Saratoga Investment Corp.

535 Madison Avenue

New York, New York 10022

Ladies and Gentlemen:

We have acted as counsel

to Saratoga Investment Corp., a Maryland corporation (the “Company”), in connection with the Company’s

registration statement on Form N-2 (File No. 333-292765) filed under the Securities Act of 1933, as amended (the “Securities

Act”), which Registration Statement was initially filed with the Securities and Exchange Commission (the “Commission”)

on January 16, 2026 (as amended as of its most recent effective date, including the exhibits and schedules thereto, all documents incorporated

or deemed to be incorporated into the Registration Statement by reference, any information contained in a prospectus supplement relating

to the Notes (as defined below) subsequently filed with the Commission pursuant to Rule 424 under the Securities Act and deemed to be

a part of the Registration Statement at the time of effectiveness pursuant to Rule 430B under the Securities Act, and any registration

statement filed pursuant to Rule 462(b) under the Securities Act, is hereinafter referred to as the “Registration Statement”)

and the Prospectus Supplement (as defined below).

The Registration Statement

relates to the public offering of securities of the Company that may be offered by the Company from time to time as set forth in the base

prospectus, dated March 11, 2026, which forms part of the Registration Statement, together with the information incorporated or deemed

to be incorporated by reference therein (the “Base Prospectus”), and as may be set forth from time to time in

one or more supplements to the Base Prospectus. This opinion letter is rendered in connection with the issuance and sale under the Securities

Act of $85,000,000 in aggregate principal amount of the Company’s 8.00% Notes due 2031 (the “Notes”),

as described in (i) the Base Prospectus and (ii) the prospectus supplement, dated August 18, 2026, relating to the Notes, together with

the information incorporated or deemed to be incorporated by reference therein (together with the Base Prospectus included therein, the

“Prospectus Supplement”), filed with the Commission pursuant to Rule 424 under the Securities Act. All of the

Notes are to be sold by the Company as described in the Registration Statement and the Prospectus Supplement.

The Notes will be issued pursuant

to the indenture, dated as of May 10, 2013 (the “Base Indenture”), by and between the Company and U.S. Bank

Trust Company, National Association (as successor in interest to U.S. Bank National Association), as trustee (the “Trustee”),

as supplemented by the eighteenth supplemental indenture, dated as of August 26, 2026 (the “Eighteenth Supplemental Indenture,”

and together with the Base Indenture, the “Indenture”), which Eighteenth Supplemental Indenture was filed by

the Company with the Commission as an exhibit to the Current Report on Form 8-K on the date hereof.

As counsel to the Company,

we have participated in the preparation of the Registration Statement, the Base Prospectus, and the Prospectus Supplement and have examined

the originals or copies, certified or otherwise identified to our satisfaction as being true copies, of the following:

(i) the Articles of Incorporation of the Company, as amended, certified as of the date hereof by an officer

of the Company;

(ii) the Third Amended and Restated Bylaws of the Company, certified as of the date hereof by an officer of

the Company;

(iii) a Certificate of Good Standing with respect to the Company issued by the State Department of Assessments

and Taxation of Maryland dated as of August 18, 2026;

(iv) the resolutions adopted by the Board of Directors of the Company (the “Board”),

or a duly authorized committee thereof, relating to, among other things: (a) the preparation and filing of the Registration Statement

and the Prospectus Supplement; (b) the offering, issuance and sale of the Notes, and the terms and conditions thereof; and (c) the authorization

of the execution and delivery of the Underwriting Agreement (as defined below) and the Indenture, certified as of the date hereof by an

officer of the Company;

(v) the Indenture;

August 26, 2026

Page 2

(vi) the Underwriting Agreement, dated as of August 18, 2026, by and among the Company and Saratoga Investment

Advisors, LLC, on the one hand, and Lucid Capital Markets, LLC, as representative of the several underwriters named in Schedule I

thereto, on the other hand (the “Underwriting Agreement”); and

(vii) a specimen copy of the form of the Notes to be issued pursuant to the Indenture in the form attached to

the Indenture.

With respect to such examination

and our opinion expressed herein, we have assumed, without any independent investigation or verification, (i) the genuineness of

all signatures on all documents submitted to us for examination, (ii) the legal capacity of all natural persons, (iii) the authenticity

of all documents submitted to us as originals, (iv) the conformity to original documents of all documents submitted to us as conformed

or reproduced copies and the authenticity of the originals of such copied documents, (v) that all certificates issued by public officials

or officers of the Company have been properly issued, (vi) the accuracy and completeness of all corporate records made available

to us by the Company, (vii) that the Indenture will be a valid and legally binding obligation of the parties thereto (other than

the Company), and (viii) that at the time of issuance of the Notes, after giving effect to such issuance, the Company will be in compliance

with Section 18(a)(1)(A) of the Investment Company Act of 1940, as amended (the “1940 Act”), giving effect to

Section 61(a)(2) of the 1940 Act.

As to certain matters of fact

relevant to the opinion in this opinion letter, we have relied on certificates of officers of the Company, and on the representations,

warranties and covenants of the Company set forth in the Underwriting Agreement. We also have relied on certificates and confirmations

of public officials (which we have assumed remain accurate as of the date of this opinion letter). We have not independently established

the facts or, in the case of certificates or confirmations of public officials, the other statements, so relied upon.

The opinion set forth below

is limited to the contract laws of the State of New York, as in effect on the date hereof, and we express no opinion with respect to any

other laws of the State of New York or the laws of any other jurisdiction. Without limiting the preceding sentence, we express no opinion

as to any state securities or broker-dealer laws or regulations thereunder relating to the offer, issuance or sale of the Notes. This

opinion letter has been prepared, and should be interpreted, in accordance with customary practice followed in the preparation of opinion

letters by lawyers who regularly give, and such customary practice followed by lawyers who on behalf of their clients regularly advise

opinion recipients regarding, opinion letters of this kind.

Based upon and subject to

the limitations, exceptions, qualifications and assumptions set forth in this opinion letter, we are of the opinion that, when the Notes

are duly executed and delivered by duly authorized officers of the Company and duly authenticated by the Trustee, all in accordance with

the provisions of the Indenture, and delivered to the purchasers thereof against payment of the agreed consideration therefor, the Notes

will constitute valid and legally binding obligations of the Company, enforceable against the Company in accordance with their terms,

except as such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, receivership, moratorium, fraudulent

conveyance, and other similar laws affecting the rights and remedies of creditors generally and by general principles of equity (including,

without limitation, the availability of specific performance or injunctive relief and the application of concepts of materiality, reasonableness,

good faith and fair dealing), regardless of whether considered in a proceeding at law or in equity.

The opinion expressed in

this opinion letter is: (i) strictly limited to the matters stated in this opinion letter, and without limiting the foregoing, no

other opinions are to be inferred; and (ii) only as of the date of this opinion letter, and we are under no obligation, and do not undertake,

to advise the Company or any other person or entity either of any change of law or fact that occurs, or of any fact that comes to our

attention, after the date of this opinion letter, even though such change or such fact may affect the legal analysis or a legal conclusion

in this opinion letter.

We hereby consent to the

filing of this opinion letter as an exhibit to the Company’s Current Report on Form 8-K, to be filed with the Commission on the

date hereof for incorporation by reference in the Registration Statement and to the reference to our firm in the “Legal Matters”

section in the Prospectus Supplement. We do not admit by giving this consent that we are in the category of persons whose consent is required

under Section 7 of the Securities Act.

Respectfully submitted,

/s/ Eversheds Sutherland (US) LLP

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