The 2026-27 MLB Offseason: Dates, Deadlines, and When to Expect Which Things (Probably)

Following the conclusion of the World Series, Major League Baseball has begun its 2026-27 offseason schedule, outlining key calendar dates, free agency deadlines, and roster decision timelines. Eligible players entered free agency immediately, opening a five-day quiet window before clubs can sign external free agents. However, looming collective bargaining agreement expiration on December 1 introduces significant uncertainty that could trigger an owner lockout and halt roster transactions.

Key dates include contract option and qualifying offer deadlines on November 2, where offers are set at $23.15 million. November 17 marks both qualifying offer responses and 40-man roster protections for the Rule 5 Draft, followed by the non-tender deadline on November 20. If an impending lockout occurs upon the CBA's expiration, major events like the Winter Meetings and Rule 5 Draft could face cancellation.