MLB’s Offseason Calendar: Every Deadline That Will Shape the Winter Market

The offseason officially began after the Milwaukee Brewers were crowned champions for the 2026 season. With the calendar turning to November, teams can now start building toward their 2027 roster.

However, this offseason is overshadowed by a potential labor dispute. With an expiring Collective Bargaining Agreement, the possibility of a protracted lockout could wreak havoc. Teams will try to get the bulk of their offseason done before a lockout pauses it.

While that is appearing more like an inevitability, teams still have some key deadlines before the CBA expires on December 1.

November 2: Deadline to Extend Qualifying Offers & Free Agency Begins

Five days after the conclusion of the World Series, teams could decide which potential free agents to extend a qualifying offer. For the 2026-2027 offseason, that value is $23.15 million. Players have until November 17, or 15 days, to decide whether to accept or reject the qualifying offer.

To be eligible for a qualifying offer, a player cannot be traded or signed after Opening Day. A player who received a qualifying offer previously in their career is forever ineligible to get a second. It's unclear how the system will go, given that there will be a new Collective Bargaining Agreement agreed upon before the next season starts.

Otherwise, free agency begins in earnest. Currently, players who have accrued six years of service time and are not under contract can test the open market. As of right now, free agents are able to talk to any team and sign a deal. There could be a free-agent frenzy ahead of December 1, as players try to find new teams before a potential lockout.

November 17: Deadline for Players to Accept or Reject a Qualifying Offer

Eight potential free agents were extended a qualifying offer for 2027. Players who accept the offer will play under a $23.15 million salary for next season. The ones who reject the offer will hit the open market.

Under the current system, teams forfeit a draft selection for signing a player who rejected a qualifying offer. For a team that receives revenue sharing, they forfeit their third-highest available selection. Other teams give up their second-highest pick. Typically, that ends up being a second-round pick, no matter the team.

Additionally, the team that loses such a free agent is entitled to draft pick compensation. That depends on the team's market size and how much a player signs for.

Six of the eight free agents who received a qualifying offer are from revenue sharing clubs. With the exception of Seiya Suzuki and David Bednar, there could be a litany of compensation picks at the end of the first round. The Yankees will only get a fourth-rounder, while the Cubs get a pick at the end of the Competitive Balance B round.

The other six free agents could net their previous club a first-rounder if they agree upon a $50 million or higher deal. All this assumes the qualifying offer system doesn't change in the next CBA, but current free agents might be grandfathered in from the current one.

November 18: Deadline to Set 40-Man Rosters Ahead of Rule 5 Draft

Perhaps the most important deadline of the offseason, teams will have to set their 40-man rosters. Usually that means a lot of tough cuts, as each MLB organization has to consider the risks of rostering or not rostering prospects.

Teams will protect prospects from the Rule 5 Draft. Players who sign out of high school or internationally at 16 have five seasons to place a minor league player on their 40-man roster. Players who are drafted out of college have four. Such players who are not on their organization's 40-man roster by this date are eligible to be selected in the Rule 5 Draft during the Winter Meetings in December.

This specific offseason could be different. A protracted lockout could result in the Rule 5 Draft being outright canceled. That would buy a year for a lot of prospects that teams are on the fence about. Some decisions could be very telling about how they feel about a potential lockout and if they really need to protect players on the bubble.

November 20: Non-Tender Deadline

Teams will have to decide whether to retain a player who is not under contract but still in his team control years. Most of the decisions revolve around players who are in their salary arbitration years, as their salaries are in the millions.

Players who accrue at least three years of service time, or the top 20% of players with two years (Super Two), are eligible for salary arbitration. However, this deadline isn't to exchange figures for 2027 salary, which comes much later. It's for teams to decide if they're worth keeping on the roster. The ones that are get tendered a contract for 2027; then the two sides negotiate a settlement or go to trial.

Sometimes, players who get bumped off the 40-man roster two days prior can show up as non-tenders. That's due to the fact the DFA process can take up to five days, and a non-tendered player can skip outright waivers and become a free agent.

December 1: Collective Bargaining Agreement Ends

This is the biggest date of the current offseason. MLB owners are expected to lock out the players if a new CBA is not reached by this date. Given the posturing of both sides, it would be a miracle if they were even close to an agreement by then.

In the event of a lockout, communication between players and teams is prohibited. That means players cannot work out in their organization's Spring Training facility with their coaching staff. That also means a freeze on transactions. It's unclear if the freeze will extend beyond 40-man roster players, but minor league players were added to the MLB Players Association between the last lockout and today.

Until an agreement is reached, the offseason is put on pause. However, until the threat of missing games becomes a possibility, it's unlikely either side will budge. Once the lockout ends, then the rest of the offseason can be completed.

Add us as a preferred source on Google