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Jan 5, 2016

Overseas Shipholding Group Announces Extension of Expiration Date of Tender Offer and Consent Solicitation for Its 7.50% Senior Notes due 2024

NEW YORK –
Overseas Shipholding Group, Inc. (NYSE MKT: OSG, OSGB) (the “Company” or
“OSG”) today announced the extension of the previously announced tender
offer (the “Tender Offer”) for any and all of its 7.50% Senior Notes due
2024 (the “Notes”) and the solicitation of consents (“Consents”) from
registered holders of the Notes (the “Consent Solicitation”) to amend
the indenture governing the Notes to affirm that for the purposes of the
restriction in such indenture on the Company’s ability to dispose of
assets, the Company’s international operations, held through its
subsidiary OSG International, Inc., do not constitute substantially an
entirety of the Company’s assets.

The Tender Offer and the Consent Solicitation have been extended by ten
days until 11:59 p.m., New York City time, on January 14, 2016. The
Tender Offer and the Consent Solicitation were previously scheduled to
expire at 11:59 p.m., New York City time, on January 4, 2016. Except as
described herein, the terms of the Tender Offer and the Consent
Solicitation remain unchanged.

The terms and conditions of the Tender Offer and the Consent
Solicitation are described in the Company’s Offer to Purchase and
Consent Solicitation Statement, dated December 2, 2015 (the
“Statement”), and the Letter of Transmittal and Consent attached
thereto, which set forth the complete terms of the Tender Offer and
Consent Solicitation.

As of 11:59 p.m., New York City time, on January 4, 2016, $204,000 in
aggregate principal amount, or approximately 29.82%, of the Notes
outstanding, excluding any outstanding Notes held by the Company or its
affiliates, has been validly tendered and not validly withdrawn. As of
such time, holders of an additional $2,000 in aggregate principal
amount, or approximately 0.29%, of the Notes outstanding, excluding any
outstanding Notes held by the Company or its affiliates, have provided
Consents that have been validly delivered and not validly revoked in the
Consent Only Option (as defined in the Statement).

Jefferies LLC is serving as the Dealer Manager for the Tender Offer and
Solicitation Agent for the Consent Solicitation. For additional
information regarding the terms of the Tender Offer and the Consent
Solicitation, please contact: Jefferies LLC at (888) 708-5831
(toll-free) or (203) 363-8273 (collect). Requests for documents may be
directed to Ipreo LLC, which is acting as Information Agent and
Depositary for the Tender Offer and the Consent Solicitation, at (888)
593-9546 (toll-free).

THIS PRESS RELEASE IS FOR INFORMATIONAL PURPOSES ONLY AND IS NOT AN
OFFER TO PURCHASE, A SOLICITATION OF AN OFFER TO PURCHASE OR A
SOLICITATION OF CONSENT WITH RESPECT TO ANY SECURITIES. THE TENDER OFFER
AND THE CONSENT SOLICITATION IS BEING MADE SOLELY PURSUANT TO THE
STATEMENT AND RELATED LETTER OF TRANSMITTAL AND CONSENT, WHICH SET FORTH
THE COMPLETE TERMS OF THE TENDER OFFER AND CONSENT SOLICITATION WHICH
HOLDERS OF THE NOTES SHOULD CAREFULLY READ PRIOR TO MAKING ANY DECISION.

THE TENDER OFFER AND THE CONSENT SOLICITATION ARE NOT BEING MADE TO
HOLDERS OF NOTES IN ANY JURISDICTION IN WHICH THE MAKING OF OR
ACCEPTANCE OF THE TENDER OFFER OR THE CONSENT SOLICITATION WOULD NOT BE
IN COMPLIANCE WITH THE LAWS OF SUCH JURISDICTION. THE COMPANY EXPRESSLY
RESERVES THE RIGHT, SUBJECT TO APPLICABLE LAW, TO TERMINATE THE TENDER
OFFER AND THE CONSENT SOLICITATION.

About OSG

Overseas Shipholding Group, Inc. (NYSE MKT: OSG, OSGB) is a publicly
traded tanker company providing energy transportation services for crude
oil and petroleum products in the U.S. and International Flag markets.
OSG is committed to setting high standards of excellence for its
quality, safety and environmental programs. OSG is recognized as one of
the world’s most customer-focused marine transportation companies and is
headquartered in New York City, NY. More information is available at www.osg.com.

Forward-Looking Statements

This release contains forward-looking statements. In addition, the
Company may make or approve certain statements in future filings with
the Securities and Exchange Commission (“SEC”), in press releases, or in
oral or written presentations by representatives of the Company. All
statements other than statements of historical facts should be
considered forward-looking statements. These matters or statements may
relate to the Company’s plans to accept for purchase Notes tendered in
the Tender Offer, to make any payments pursuant to the terms of the
Tender Offer and the Consent Solicitation and to amend the indenture
governing the Notes. Forward-looking statements are based on the
Company’s current plans, estimates and projections, and are subject to
change based on a number of factors. Investors should carefully consider
the risk factors outlined in more detail in the Company’s Annual Report
for 2014 on Form 10-K under the caption “Risk Factors” and in similar
sections of other filings made by the Company with the SEC from time to
time. The Company assumes no obligation to update or revise any
forward-looking statements. Forward-looking statements and written and
oral forward looking statements attributable to the Company or its
representatives after the date of this release are qualified in their
entirety by the cautionary statements contained in this paragraph and in
other reports previously or hereafter filed by the Company with the SEC.

Investor Relations & Media:
Overseas Shipholding Group,
Inc.
Brian Tanner, 212-578-1645
btanner@osg.com