Chicago Cubs 2026–2027 Offseason Guide: Important Dates, Roster Decisions & Calendar

This guide provides a comprehensive overview of the Cubs 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 Cubs enter the 2026–2027 offseason with major decisions across the roster. Some of those decisions include the free agency decisions to retain or let go of Seiya Suzuki and Ian Happ, rebuilding the starting rotation and bullpen, and sorting through contract options. This will help determine what Chicago looks like when baseball returns to Wrigley Field.

This guide covers the dates Cubs fans need to know, from free agency and roster deadlines to Cubs Convention and the scheduled start of the 2027 season.

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 so fans can distinguish the published schedule from any eventual changes.

Important Dates at a Glance

• Day after the World Series ends: Eligible Cubs 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 / 10:59 p.m. Central: Current collective bargaining agreement expires.
• December 2026: December 7–9 is the reported baseball-business schedule; published calendars differ on the full meeting window. — pending lockout.
• 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.
• January 15–17: Cubs Convention at the Sheraton Grand Chicago.
• Late January–February: Expected arbitration hearings — pending lockout.
• February: Cubs pitchers, catchers, and position players report; exact dates unannounced — pending lockout.
• February 19: Scheduled Cubs spring opener against the Athletics in Mesa — pending lockout.
• February 20: Scheduled Sloan Park opener against Cincinnati — pending lockout.
• March: Spring Breakout details unannounced — pending lockout.
• March 24: Scheduled MLB Opening Night; matchup unannounced — pending lockout.
• March 25: Scheduled Cubs Opening Day and home opener against Cleveland at Wrigley Field — pending lockout.

Free Agency: Who Could Leave the Cubs?

The end of the World Series starts the countdown to Chicago’s first major decisions. Eligible players become free agents the following day, with their former club retaining an initial exclusive negotiating period.

Game 7 is scheduled for October 31. If the series goes the distance without a schedule change, players would become free agents on November 1, and the five-day window would end on November 5. An earlier finish moves those deadlines forward.

Chicago’s pending free agents include:

• Outfield: Seiya Suzuki, Ian Happ, Tyrone Taylor, and Michael Conforto.
• Starting pitching: Shota Imanaga, Kevin Gausman, and David Peterson.
• Additional pitching: Aaron Civale and Trent Thornton.

Tyler Austin's (remember him?) status also requires attention because his contract and remaining club control complicate a straightforward free-agent designation. Players with options are listed separately below.

For the Cubs, the central questions are how much of the outfield to retain and how many experienced starters to bring back. Losing multiple contributors at once would put added pressure on both the free-agent market and Chicago’s internal replacements.

View our top free agents ranking by clicking here.

Contract Options: The Cubs’ Decisions

It should be noted that none of these decisions have been made yet. Mutual options require both sides to agree, while Holmes controls his player option and the Cubs control the club options.

Assad’s situation deserves particular attention: declining his option would not automatically make him a free agent. The Cubs could retain him through arbitration if they tender him a contract.

Option deadlines follow individual contracts. Decisions should be updated when officially announced.

Qualifying Offers

The reported qualifying offer for the 2026–2027 offseason is $23.15 million for one season, according to the New York Post. Teams must extend offers by the fifth day after the World Series; the reported acceptance deadline is November 17.

Suzuki and Happ are the principal Cubs decisions to watch, with Boyd another potential candidate if he reaches free agency.

Imanaga is ineligible to receive another qualifying offer after accepting one last offseason. Players acquired during the season, including Gausman, Holmes, and Peterson, are also ineligible to receive the QO.

For Chicago, an offer creates two possible outcomes: retaining a player on a one-year contract if he accepts, or potentially receiving draft compensation if he declines and signs elsewhere under the applicable rules.

General Manager Meetings: November 9–12

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

This is an early opportunity for the Cubs to pursue pitching, gauge the market for their own free agents, and explore trades. 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, 2026.

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

The Cubs must decide which eligible prospects warrant places on the 40-man roster. Right-hander Jaxon Wiggins is a notable name to monitor, provided he has not already been added before the deadline. Being eligible for protection does not mean a roster move has been announced.

The November protection deadline comes before the agreement expires. It should remain distinct from the December draft, which could be affected by a work stoppage.

Awards Season

November brings announcements for defense, offense, pitching, and overall performance:

• 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.

Cubs finalists, voting finishes, and winners should be added as announcements become official. The MLB Awards celebration and the individual BBWAA announcements are separate parts of the calendar.

Non-Tenders and Arbitration

Non-tender deadline: November 20.

Scheduled arbitration figure exchange: January 8 — pending lockout.

Expected hearings: late January–February — pending lockout.

Chicago’s arbitration group includes Justin Steele, Edward Cabrera, Braxton Garrett, Javier Assad, Miguel Amaya, Gabriel Arias, Ryan Rolison, Ethan Roberts, Michael Busch, Ben Brown, and Daniel Palencia.

Assad’s participation depends on his option decision. Any published salary projections remain estimates until the Cubs and player reach an agreement or an arbitration panel issues a decision.

Tendering a contract retains a player’s rights; it does not mean the sides have agreed on his salary.

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.

These events could be postponed or altered. They should not be described as officially canceled unless MLB announces that decision.

The Cubs’ final 2027 draft position, compensation selections, and bonus allocations should be added when official. Competitive Balance selections belong in the guide only where they directly affect Chicago, including any subsequent trade. Unconfirmed allocations and selections remain pending lockout.

Cubs Convention: January 15–17, 2027

The 2027 Cubs Convention is announced for January 15–17 at the Sheraton Grand Chicago. Programming and participation details will be released separately.

The announced event dates belong on the calendar even while the baseball schedule faces labor uncertainty. Any changes to player participation or programming should follow the club’s updates.

Hall of Fame Voting: A Cubs Connection

The 2027 ballot offers a familiar storyline for Cubs fans, with Jon Lester, Jake Arrieta, and Wade Davis among the potential first-year candidates. Former Cubs pitcher Cole Hamels is among the returning candidates. Ballot inclusion and results should follow the official announcements.

The exact January results date has not been verified for this guide. Hall of Fame voting operates separately from MLB roster business, so an unannounced election date should not be presented as a confirmed lockout postponement.

International Signing Period

Expected opening: January 15, 2027 — pending lockout.

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

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

Spring Training in Mesa

Reporting dates: pending lockout.

The Cubs’ published exhibition schedule begins February 19 against the Athletics in Mesa, followed by the Sloan Park opener against the Reds on February 20. Both dates are pending lockout.

Other scheduled Sloan Park games include the White Sox on February 23, the Dodgers on March 15, and the Brewers on March 22–23. All are pending lockout. First-pitch times, reporting dates, and Spring Breakout details should be updated as announced.

Opening Day at Wrigley Field

The Cubs are scheduled to open the 2027 season Thursday, March 25, against the Cleveland Guardians at Wrigley Field — pending lockout. First-pitch time and broadcast details remain subject to announcement.

Before that first pitch, Chicago faces a winter that could reshape its rotation, outfield, and bullpen. This guide will be updated as contract decisions become official, dates are confirmed, and labor negotiations determine the path to the 2027 season.