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May 3, 2016

Overseas Shipholding Group to Announce First Quarter 2016 Results on May 10, 2016

NEW YORK –
Overseas Shipholding Group, Inc. (NYSE MKT:OSG)(NYSE MKT:OSGB) (the
“Company” or “OSG”) today announced that it plans to release first
quarter 2016 results before market open on Tuesday, May 10, 2016.

The Company will host a conference call to discuss its first quarter
2016 results at 9:00 a.m. ET on Tuesday, May 10, 2016.

To access the call, participants should dial (866) 490-3149 for domestic
callers and (707) 294-1567 for international callers. Please dial in ten
minutes prior to the start of the call and enter Conference ID 3193934.

A live webcast of the conference call will be available from the
Investor Relations section of the Company’s website at http://www.osg.com/.

An audio replay of the conference call will be available starting at
12:00 p.m. ET on Tuesday, May 10, 2016 through 11:59 p.m. ET on Tuesday,
May 17, 2016 by dialing (855) 859-2056 for domestic callers and (404)
537-3406 for international callers, and entering Conference ID 3193934.

About OSG

Overseas Shipholding Group, Inc. (NYSE MKT:OSG)(NYSE MKT: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, in press releases, or 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 prospects, including statements regarding trends in the
tanker and articulated tug/barge markets, and possibilities of certain
strategic alliances and investments. These statements are based on
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
2015 on Form 10-K and in other reports hereafter filed by the Company
with the SEC under the caption “Risk Factors.” 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 statement
contained in this paragraph and in other reports hereafter filed by the
Company with the SEC.

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