Exhibit 99.1

OVERSEAS SHIPHOLDING GROUP REPORTS

SECOND QUARTER 2021 RESULTS

Tampa, FL – August 6, 2021 – Overseas Shipholding Group, Inc. (NYSE: OSG) (the “Company” or “OSG”), a leading provider of energy transportation services for crude oil and petroleum products in the U.S. Flag markets, today reported results for the second quarter 2021.

Sam Norton, President and CEO, commenting on the recently completed quarter, stated “OSG’s financial performance this quarter offers evidence of improving fundamentals in our core markets. Continued solid cash flows generated by our niche and ATC assets combined with stable contributions from our conventional tanker and ATB fleets to deliver better than anticipated EBITDA. The recovery slope of domestic marine transportation demand has been flatter than what had been expected earlier in the year due to import substitution for domestic supply. When fuel demand patterns consistent with historic levels of consumption normalize in the quarters ahead, we believe this will stimulate more marine transportation demand, which would positively impact our financial results.”

Mr. Norton added, “The ongoing global coronavirus pandemic continues to weigh on demand and transport pricing dynamics in the global liquid bulk transportation markets. Our customers’ reluctance to enter into longer-term transportation commitments has been a continuing condition since the onset of the pandemic. As vaccines become more widely distributed globally and consumption of transportation fuels outside of the United States regains traction, demand for Jones Act tankers domestically should normalize as our customers’ visibility toward and confidence in the future returns.”

^{A, B, C} Reconciliations of these non-GAAP financial measures are included in the financial tables attached to this press release starting on Page 8.

Second Quarter 2021 Results

Shipping revenues were $88.4 million for the quarter, an increase of $7.1 million, or 8.7%, from the first quarter of 2021. TCE revenues increased $6.2 million, or 9.4%, from the first quarter to $71.7 million in the second quarter. The revenue increase was driven by increases in lightering volumes and a 58-day increase in chartered out days during the second quarter.

The second quarter operating loss was $5.8 million compared to the first quarter operating loss of $15.7 million. The first quarter loss included a provision for loss related to the sale of the Overseas Gulf Coast of $5.5 million.

Quarterly adjusted EBITDA increased to $10.2 million during the second quarter, a $4 million increase from the first quarter of 2021. The increase was driven by the increased revenues for the quarter.

Shipping revenues were $88.4 million for the quarter, down 22.9% compared with the second quarter of 2020. TCE revenues for the second quarter of 2021 were $71.7 million, a decrease of $28.7 million, or 28.6%, compared with the second quarter of 2020, primarily a result of a 599-day increase in lay-up days due to seven vessels in lay-up, a decision taken in light of the lack of demand due to the economic impact of COVID-19.

Operating loss for the second quarter of 2021 was $5.8 million compared to operating income of $13.6 million in the second quarter of 2020.

Net loss for the second quarter of 2021 was $10.7 million, or $(0.12) per diluted share, compared with net income of $6.4 million, or $0.07 per diluted share, for the second quarter 2020.

Adjusted EBITDA was $10.2 million for the quarter, a decrease of $19.6 million compared with the second quarter of 2020, driven primarily by the decrease in TCE revenues.

Conference Call

The Company will host a conference call to discuss its second quarter 2021 results at 9:30 a.m. Eastern Time (“ET”) on Friday, August 6, 2021.

To access the call, participants should dial (844) 850-0546 for domestic callers and (412) 317-5203 for international callers. Please dial in ten minutes prior to the start of the call.

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 11:30 a.m. ET on Friday, August 6, 2021 through 10:59 p.m. ET on Friday, August 13, 2021 by dialing (877) 344-7529 for domestic callers and (412) 317-0088 for international callers, and entering Access Code 10158907.

About Overseas Shipholding Group, Inc.

Overseas Shipholding Group, Inc. (NYSE:OSG) is a publicly traded company providing energy transportation services for crude oil and petroleum products in the U.S. Flag markets. OSG is a major operator of tankers and ATBs in the Jones Act industry. OSG’s 22 vessel U.S. Flag fleet consists of three crude oil tankers doing business in Alaska, two conventional ATBs, two lightering ATBs, three shuttle tankers, ten MR tankers, and two non-Jones Act MR tankers that participate in the U.S. Maritime Security Program. OSG also currently owns and operates one Marshall Islands flagged MR tanker which trades internationally.

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 Tampa, FL. More information is available at www.osg.com.

Forward-Looking Statements

This press release contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. In addition, the Company may make or approve certain forward-looking 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 our prospects, supply and demand for vessels in the markets in which we operate and the impact on market rates and vessel earnings, the continued stability of our niche businesses, and the impact of our time charter contracts on our future financial performance. Forward-looking statements are based on our current plans, estimates and projections, and are subject to change based on a number of factors. COVID-19 has had, and will continue to have, a profound impact on our workforce and many other aspects of our business and industry. Investors should carefully consider the risk factors outlined in more detail in our filings with the SEC. We do not assume any obligation to update or revise any forward-looking statements except as may be required by applicable law. Forward-looking statements and written and oral forward-looking statements attributable to us or our representatives after the date of this press release are qualified in their entirety by the cautionary statements contained in this paragraph and in other reports previously or hereafter filed by us with the SEC.

Investor Relations & Media Contact:

Susan Allan, Overseas Shipholding Group, Inc.

(813) 209-0620

sallan@osg.com

Consolidated Statements of Operations

($ in thousands, except per share amounts)

Consolidated Balance Sheets

($ in thousands)

Consolidated Statements of Cash Flows

($ in thousands)

Spot and Fixed TCE Rates Achieved and Revenue Days

The following tables provide a breakdown of TCE rates achieved for spot and fixed charters and the related revenue days for the three and six months ended June 30, 2021 and the comparable periods of 2020. Revenue days in the quarter ended June 30, 2021 totaled 1,484 compared with 2,031 in the prior year quarter.

(a) Excludes one Alaska vessel currently in layup.

Fleet Information

As of June 30, 2021, OSG’s operating fleet consisted of 24 vessels, 12 of which were owned, with the remaining vessels chartered-in. Vessels chartered-in are on Bareboat Charters.

Reconciliation to Non-GAAP Financial Information

The Company believes that, in addition to conventional measures prepared in accordance with GAAP, the following non-GAAP measures provide investors with additional information that will better enable them to evaluate the Company’s performance. Accordingly, these non-GAAP measures are intended to provide supplemental information, and should not be considered in isolation or as a substitute for measures of performance prepared with GAAP.

(A) Time Charter Equivalent (TCE) Revenues

Consistent with general practice in the shipping industry, the Company uses TCE revenues, which represents shipping revenues less voyage expenses, as a measure to compare revenue generated from a voyage charter to revenue generated from a time charter. TCE revenues, a non-GAAP measure, provides additional meaningful information in conjunction with shipping revenues, the most directly comparable GAAP measure, because it assists Company management in making decisions regarding the deployment and use of its vessels and in evaluating their financial performance. Reconciliation of TCE revenues of the segments to shipping revenues as reported in the consolidated statements of operations follows:

Vessel Operating Contribution

Vessel operating contribution, a non-GAAP measure, is TCE revenues minus vessel expenses and charter hire expenses.

(B) EBITDA and Adjusted EBITDA

EBITDA represents net income/(loss) before interest expense, income taxes and depreciation and amortization expense. Adjusted EBITDA consists of EBITDA adjusted to exclude amortization classified in charter hire expenses, interest expense classified in charter hire expenses, loss/(gain) on disposal of vessels and other property, including impairments, net, non-cash stock based compensation expense and loss on repurchases and extinguishment of debt and the impact of other items that we do not consider indicative of our ongoing operating performance. EBITDA and Adjusted EBITDA do not represent, and should not be a substitute for, net income/(loss) or cash flows from operations as determined in accordance with GAAP. Some of the limitations are: (i) EBITDA and Adjusted EBITDA do not reflect our cash expenditures, or future requirements for capital expenditures or contractual commitments; (ii) EBITDA and Adjusted EBITDA do not reflect changes in, or cash requirements for, our working capital needs; and (iii) EBITDA and Adjusted EBITDA do not reflect the interest expense, or the cash requirements necessary to service interest or principal payments, on our debt. While EBITDA and Adjusted EBITDA are frequently used as a measure of operating results and performance, neither of them is necessarily comparable to other similarly titled measures used by other companies due to differences in methods of calculation. The following table reconciles net income/(loss) as reflected in the consolidated statements of operations, to EBITDA and Adjusted EBITDA.

(C) Total Cash