Exhibit 99.1

OVERSEAS SHIPHOLDING GROUP REPORTS

THIRD QUARTER 2021 RESULTS

Tampa, FL – November 9, 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 third quarter 2021.

Sam Norton, President and CEO, commenting on the recently completed quarter, stated, “Most notable of today’s announced financial results was the continued sequential improvement in quarter-to-quarter EBITDA performance. Vessels in operation performed well during the third quarter, providing solid cashflow in a market environment that has continued to be beset with high levels of uncertainty. In recent weeks, two vessels have been re-activated and rejoined the operating fleet. We are optimistic that this trend will continue as Jones Act vessel availability across the fourth quarter and into 2022 tightens. At this time, all of OSG’s active vessels will be operating under time charter into the first quarter of 2022. Current conditions provide strong support for re-activating additional laid-up vessels by year end, providing optimism that sequentially improving quarter to quarter EBITDA performance is attainable over the next six months.”

Mr. Norton added, “Having bolstered our liquidity position with the completion of our refinancing at the end of the third quarter, OSG is now well positioned to pursue opportunities in what we continue to see as an improving market environment. Global energy markets are on track to regain pre-COVID consumption levels by early next year, with demand signals indicating a rising need for transportation capacity. Increased international air travel in the months ahead, in particular, should add to firming market demand. We remain optimistic that a return to more normalized market conditions lies ahead in 2022.”

^{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.

Third Quarter 2021 Results

Shipping revenues were $94.0 million for the quarter, an increase of $5.6 million, or 6.3%, from the second quarter of 2021. TCE revenues increased $3.7 million, or 5.1%, from the second quarter to $75.4 million in the third quarter. The revenue increase was primarily a result of a 23-day decrease in scheduled drydocking and a 38-day decrease in lay-up days, as two of seven vessels came out of lay-up during the third quarter of 2021.

The third quarter operating loss was $5.6 million compared to the second quarter operating loss of $5.8 million.

Quarterly adjusted EBITDA increased to $12.2 million during the third quarter, a $2.0 million increase from the second quarter of 2021. The increase was driven by the increased revenues for the quarter.

Shipping revenues were $94.0 million for the quarter, down 11.1% compared with the third quarter of 2020. TCE revenues for the third quarter of 2021 were $75.4 million, a decrease of $16.9 million, or 18.3%, compared with the third quarter of 2020, primarily a result of a 498-day increase in lay-up days due to vessels in lay-up during the third quarter of 2021 and one less MR tanker in the Company’s fleet, Overseas Gulf Coast, which was sold during the second quarter of 2021. The decrease was offset by (a) the addition to the Company’s fleet of one ATB, OSG 205 and OSG Courageous, which was delivered during the fourth quarter of 2020, (b) a 171-day decrease in scheduled drydocking and (c) an increase in Delaware Bay lightering volumes.

Operating loss for the third quarter of 2021 was $5.6 million compared to operating income of $5.2 million for the third quarter of 2020.

Net loss for the third quarter of 2021 was $16.0 million, or $(0.18) per diluted share, compared with net loss of $0.7 million, or $(0.01) per diluted share, for the third quarter 2020. During the third quarter of 2021, the Company recognized an aggregate net loss of $8.0 million on extinguishment of debt, which reflects a write-off of unamortized deferred financing costs and prepayment fees and an impairment charge of $1.0 million on two of the Company's leased vessels.

Adjusted EBITDA was $12.2 million for the quarter, a decrease of $9.6 million compared with the third quarter of 2020, driven primarily by the decrease in TCE revenues.

Conference Call

The Company will host a conference call to discuss its third quarter 2021 results at 10:00 a.m. Eastern Time (“ET”) on Tuesday, November 9, 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 12:00 p.m. ET on Tuesday, November 9, 2021 through 10:59 p.m. ET on Tuesday, November 16, 2021 by dialing (877) 344-7529 for domestic callers and (412) 317-0088 for international callers, and entering Access Code 10161526.

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 nine months ended September 30, 2021 and the comparable periods of 2020. Revenue days in the quarter ended September 30, 2021 totaled 1,494 compared with 1,874 in the prior year quarter.

(a) Excludes one Alaska vessel currently in layup.

Fleet Information

As of September 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