Exhibit 99.1

OVERSEAS SHIPHOLDING GROUP REPORTS

THIRD QUARTER 2022 RESULTS

Tampa, FL – November 3, 2022 – 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 2022.

Sam Norton, President and CEO, offered the following comments on the quarterly results announced today: “Financial results achieved during the past quarter provide a welcome affirmation of our long-held belief in the viability of OSG’s business strategy, exceeding our expectations and signaling continued strength through the balance of the year and into 2023. Our niche businesses in particular delivered stellar results for the quarter, adding meaningfully to the continuing rebound seen in the time charter equivalent returns of our conventional tankers and ATBs. Adjusted EBITDA of $42.3 million generated $14 million of free cashflow for the period, clearly the best performance on that measure in many years.”

Mr. Norton added, “As previously announced, redelivery in December of three conventional tankers will reduce the number of vessels leased from American Shipping Company, releasing OSG from annual fixed payment obligations of approximately $27 million during 2023 and beyond. The effective deleveraging achieved through the decision not to extend options on these three vessels should, when taken together with positive free cash flow performance expected in the quarters ahead, provide OSG with enhanced flexibility to address existing and anticipated business opportunities.”

^{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 2022 Results

Shipping revenues were $123.6 million for the third quarter of 2022, an increase of $5.1 million, or 4.3%, from the second quarter of 2022. TCE revenues increased $11.8 million, or 11.4%, from the second quarter of 2022 to $115.1 million in the third quarter of 2022. The increases were primarily a result of (a) an 82-day decrease in layup days, as our two remaining vessels in layup returned to service in May 2022, (b) an increase in average daily rates earned by our fleet and (c) a 10-day decrease in repair days. The increases were partially offset by (a) a 13-day increase in scheduled drydocking, (b) a decrease in Delaware Bay lightering volumes and (c) the timing of Government of Israel voyages.

Third quarter 2022 operating income was $22.4 million compared to the second quarter 2022 operating income of $12.6 million.

Quarterly adjusted EBITDA increased to $42.3 million during the third quarter of 2022, a $10.8 million increase from the second quarter of 2022. The increase was driven by the increased revenues for the quarter.

In comparison to the third quarter of 2021, shipping revenues were up 31.0% and TCE revenues increased $39.7 million or 52.7%. The increases primarily resulted from a 599-day decrease in layup days as we had no vessels in layup. During the third quarter of 2021, we had seven vessels in layup for most of the quarter with two of seven vessels coming out of layup in September 2021. Additionally, the increase in TCE revenues resulted from an increase in average daily rates earned by our fleet and an increase in Delaware Bay lightering volumes. The increase was partially offset by a 54-day increase in scheduled drydocking.

Operating income for the third quarter of 2022 was $22.4 million compared to an operating loss of $5.6 million for the third quarter of 2021. Net income for the third quarter of 2022 was $13.2 million, or $0.15 per diluted share, compared with a net loss of $16.0 million, or $(0.18) per diluted share, for the third quarter of 2021.

Adjusted EBITDA was $42.3 million for the 2022 third quarter, an increase of $30.1 million compared with the third quarter of 2021, driven primarily by the increase in TCE revenues.

Conference Call

The Company will host a conference call to discuss its third quarter 2022 results at 9:30 a.m. Eastern Time (“ET”) on Friday, November 4, 2022.

To access the call, participants should dial (844) 200-6205 for domestic callers and (929) 526-1599 for international callers and enter Access Code 947417. 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 www.osg.com.

An audio replay of the conference call will be available for one week starting at 11:30 a.m. ET on Friday, November 4, 2022, by dialing (866) 813-9403 for domestic callers and (929) 458-6194 for international callers and entering Access Code 291009.

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 23 vessel U.S. Flag fleet consists of three Suezmax 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, and one tanker in cold layup. In addition, OSG also 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 fact 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, the impact of our time charter contracts on our future financial performance, and external events including geopolitical conflicts such as the Russian/Ukraine conflict. 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, 2022 and the comparable period of 2021. Revenue days in the quarter ended September 30, 2022 totaled 2,035 compared with 1,494 in the prior year quarter.

(a) Excludes one Alaska vessel currently in layup.

Fleet Information

As of September 30, 2022, 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