NEW YORK –
Overseas Shipholding Group, Inc. (NYSE MKT:OSG, OSGB) (the “Company” or
“OSG”) today announced the further 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 “Proposed
Amendment”).

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.

On January 5, 2016, the Company announced that the expiration date of
the Tender Offer and the Consent Solicitation had 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 have been further extended by
five business days until 11:59 p.m., New York City time, on January 22,
2016 (the “Expiration Time”). Additionally, the Company has waived the
condition to the Tender Offer requiring the execution of a supplemental
indenture effecting the Proposed Amendment and intends to accept for
purchase all Notes validly tendered and not validly withdrawn prior to
the Expiration Time. The Withdrawal Deadline (as defined in the
Statement) has also been extended until 11:59 p.m., New York City time,
on January 22, 2016. Except as described herein, the terms of the Tender
Offer and the Consent Solicitation remain unchanged.

As of 5:00 p.m., New York City time, on January 14, 2016, $294,000 in
aggregate principal amount, or approximately 42.98%, 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affiliates, has been validly tendered and not validly withdrawn.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 $52,000 in aggregate principal
amount, or approximately 7.60%, 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.

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