Boston Red Sox 2026–2027 Offseason Guide: Important Dates, Roster Decisions & Calendar

This guide provides a comprehensive overview of the Red Sox 2026-2027 offseason schedule, highlighting essential dates for the Winter Meetings, MLB Draft Lottery, and key decision-making periods for arbitration-eligible players and those with team or mutual contract options.

The Red Sox enter the 2026–2027 offseason with a relatively small group of potential free-agent departures and a much larger set of arbitration decisions. Sonny Gray’s contract, Garrett Whitlock’s club option, and the cost and fit of Boston’s returning players will shape the winter.

This guide covers free agency, contract options, roster protection, awards, the Winter Meetings, and the scheduled return of baseball to Fenway Park.

Calendar note: MLB’s current collective bargaining agreement expires December 1, 2026, at 11:59 p.m. Eastern. A lockout is anticipated but has not begun. Events and baseball operations that could be affected are marked “pending lockout.” Announced dates remain listed unless officially changed.

Important Dates at a Glance

• Day after the World Series ends: Eligible Red Sox become free agents; offseason trades resume under the current agreement.
• Fifth day after the World Series ends: Exclusive negotiating period ends; eligible free agents can sign with other clubs. Qualifying offers are due. Individual contract-option deadlines must also be checked.
• November 1, 2026: Gold Glove Award winners announced.
• November 2: BBWAA award finalists and Silver Slugger finalists announced.
• November 9–12: General Manager Meetings in Las Vegas.
• November 9: Rookie of the Year winners announced.
• November 10: Manager of the Year winners announced.
• November 11: Cy Young Award winners announced; MLB Awards celebration in Las Vegas.
• November 12: Most Valuable Player Award winners announced.
• November 17: Rule 5 roster protection deadline; qualifying-offer acceptance deadline; Silver Slugger winners announced.
• November 20: Non-tender deadline.
• December 1, 11:59 p.m. Eastern: Current collective bargaining agreement expires.
• December 2026: Winter Meetings — pending lockout. December 7–9 is the reported baseball-business schedule; published calendars differ on the full meeting window.
• December 8: Scheduled MLB Draft Lottery — pending lockout.
• December 9: Scheduled Major League Rule 5 Draft — pending lockout.
• January 8, 2027: Scheduled salary arbitration figure exchange — pending lockout.
• January 15: Expected international signing period opening under the existing system — pending lockout.
• Late January–February: Expected arbitration hearings — pending lockout.
• February: Red Sox pitchers, catchers, and position players report to Fort Myers; exact dates unannounced — pending lockout.
• February 19: Scheduled exhibition against Northeastern University at JetBlue Park — pending lockout.
• February 20: Scheduled Grapefruit League opener at Tampa Bay — pending lockout.
• February 21: Scheduled Grapefruit League home opener against Minnesota — pending lockout.
• March: Spring Breakout details unannounced — pending lockout.
• March 22–23: Scheduled exhibitions against San Francisco at Oracle Park — pending lockout.
• March 24: Scheduled MLB Opening Night; matchup unannounced — pending lockout.
• March 25: Scheduled Red Sox Opening Day at Seattle — pending lockout.
• April 1: Scheduled home opener against Cincinnati at Fenway Park — pending lockout.

Free Agency: Who Could Leave Boston?

Boston’s principal unrestricted free agents are:

• LHP Patrick Sandoval.
• INF Isiah Kiner-Falefa.

Two additional players can reach the market through contract-option decisions:

• RHP Sonny Gray: Mutual option.
• RHP Garrett Whitlock: Club option.

These situations should remain separate until the options are resolved. Gray and Whitlock are not automatically free agents simply because an option decision is approaching.

Boston’s winter is about deciding how to improve its offense, maintain pitching depth, and make room for the players it wants to carry into 2027 with the lack of turnover on the roster coming.

View our top free agents ranking by clicking here.

Contract Options: Gray, Whitlock, and Chapman

• Sonny Gray: $30 million mutual option for 2027.
• Garrett Whitlock: Approximately $8.3 million club option for 2027.
• Aroldis Chapman: His 2027 option has reportedly vested, making his situation different from an unresolved mutual-option decision.

Gray’s option requires both sides to agree. If it is declined, Boston could still negotiate a new contract with him. Whitlock’s decision rests with the club.

Chapman’s option reportedly became guaranteed after he met the innings and physical requirements.

Individual contract deadlines should be checked separately from the league’s general free-agency calendar.

Qualifying Offers

The reported qualifying offer is $23.15 million for one season, according to the New York Post. Offers are due on the fifth day after the World Series, with the reported acceptance deadline on November 17.

Boston must evaluate both eligibility and value before extending an offer. Under the current rules, players cannot receive a second qualifying offer, and players acquired during the season cannot receive one from their new club.

The system also affects outside additions. Pursuing a free agent who rejected an offer can carry draft and international signing consequences under the applicable rules. No potential Red Sox offer should be described as official before the club announces it.

General Manager Meetings: November 9–12

The GM Meetings take place in Las Vegas from November 9–12.

For Boston, the meetings provide an early opportunity to discuss offensive upgrades, assess the market for pitching, and explore trades that could address roster overlap.

The approaching expiration of the labor agreement could encourage earlier negotiations and deals, although it does not guarantee a rush of completed deals.

Rule 5 Protection and the 40-Man Roster

Protection deadline: November 17.

Scheduled Major League Rule 5 Draft: December 9 — pending lockout.

Boston prospects listed as eligible for the December 2026 Rule 5 Draft include:

• OF Miguel Bleis.
• INF Mikey Romero.
• C Brooks Brannon.
• C Johanfran Garcia.
• LHP Hayden Mullins.
• RHP Blake Wehunt.

These are eligibility and protection decisions, not announced roster additions. Their status should be checked against the current 40-man roster before the deadline.

The challenge is balancing prospect protection with the immediate needs of the Major League roster. Keeping an additional veteran can reduce the space available for a prospect, while protecting a player can require another transaction.

The November protection deadline precedes the expiration of the labor agreement. The December draft remains pending lockout.

Awards Season

Boston fans can follow the major announcements throughout November:

• November 1: Gold Glove winners.
• November 2: BBWAA award finalists and Silver Slugger finalists.
• November 9: Rookie of the Year.
• November 10: Manager of the Year.
• November 11: Cy Young Awards and the MLB Awards celebration.
• November 12: Most Valuable Player.
• November 17: Silver Slugger winners.

Red Sox finalists, voting finishes, and winners should be added as announced. The MLB Awards celebration and individual BBWAA announcements are separate events.

Non-Tenders and Arbitration

Non-tender deadline: November 20.

Scheduled figure exchange: January 8 — pending lockout.

Expected hearings: late January–February — pending lockout.

Boston’s reported arbitration group includes:

• Position players: Wilyer Abreu, Triston Casas, Jarren Duran, Romy Gonzalez, Jahmai Jones, Andruw Monasterio, Adley Rutschman, Eli White, and Connor Wong.
• Pitchers: Kutter Crawford, Tyron Guerrero, Tanner Houck, Zack Kelly, Erik Miller, Johan Oviedo, Justin Slaten, and Greg Weissert.

Among the larger published salary projections are Duran at $11.1 million, Rutschman at $9.1 million, Abreu at $4.6 million, and Houck at $4.1 million. These are estimates, not agreed salaries.

The size of this group makes the tender deadline a significant roster checkpoint. Boston must weigh each player’s expected salary, health, role, and available alternatives.

Tendering a contract retains a player’s rights. Salary negotiations can continue afterward.

Winter Meetings, Draft Lottery, and Competitive Balance Picks

Winter Meetings: December — pending lockout.

Scheduled Draft Lottery: December 8 — pending lockout.

Scheduled Major League Rule 5 Draft: December 9 — pending lockout.

Boston’s final draft position, compensation adjustments, and bonus allocations should be added when official. The lottery is a league calendar event; its presence here does not establish that Boston is eligible to participate.

Competitive Balance selections should be included only where they directly affect the Red Sox, including any trade. Unconfirmed arrangements remain pending lockout.

These events should not be described as officially canceled without an MLB announcement.

Hall of Fame Voting: Lester and Pedroia

The 2027 ballot provides two major Boston storylines:

• Jon Lester: A prominent first-year candidate and a key member of Boston’s 2007 and 2013 championship teams.
• Dustin Pedroia: A returning candidate whose case remains closely connected to his career with the Red Sox.

Other potential newcomers with Boston ties include Andrew Miller and Pablo Sandoval.

The exact January results date has not been verified for this guide. Hall of Fame voting operates separately from MLB roster business.

International Signing Period

Expected opening: January 15, 2027 — pending lockout.

There has been no word as of yet on how much the Red Sox international bonus pool will be for 2027.

This is another opportunity for the Red Sox to build long-term depth alongside the domestic draft and player development system.

Spring Training in Fort Myers

Reporting dates: pending lockout.

Boston’s scheduled opening sequence is:

• February 19: Exhibition against Northeastern University at JetBlue Park — pending lockout.
• February 20: Grapefruit League opener at Tampa Bay in Port Charlotte — pending lockout.
• February 21: Grapefruit League home opener against Minnesota at JetBlue Park — pending lockout.

The Red Sox are also scheduled to finish their exhibition schedule with games against the Giants at Oracle Park on March 22–23 — pending lockout.

Spring Training will provide a clearer picture of Boston’s pitching health, bench construction, and competition for at-bats. Game times, reporting dates, and Spring Breakout details should be added as announced.

Opening Day and the Return to Fenway Park

March 25: Scheduled Red Sox season opener at Seattle — pending lockout.

April 1: Scheduled home opener against Cincinnati at Fenway Park — pending lockout.

First-pitch times and broadcast information remain subject to announcement.

Boston’s winter will be shaped by the decisions surrounding its returning roster as much as its new additions. Resolving the pitching options, managing arbitration costs, and improving the lineup will determine how the Red Sox approach the 2027 season.