With MLB season complete, here are the key dates to know for the Red Sox’ offseason

The Boston Red Sox and Major League Baseball face an urgent offseason calendar ahead of an expected lockout when the collective bargaining agreement expires on December 1, 2026. This impending labor stoppage creates a tight transaction window for Chief Baseball Officer Craig Breslow and the front office. Key early dates include the general managers' meetings in Las Vegas from November 9 to 12 and the qualifying offer decision deadline on November 12.

Additional key roster deadlines arrive later in November, including the 40-man roster protection cutoff on November 17 and the contract tender deadline on November 20. Boston must make critical roster choices, with players like Braiden Ward and Mikey Romero eligible for the Rule 5 draft, alongside a large arbitration-eligible class including Jarren Duran, Tanner Houck, and Triston Casas before transactions pause on December 1.