Important dates for Cubs fans to know in the 2025-26 MLB offseason

The Chicago Cubs' 2025 season wrapped up last week with a tough loss to the Milwaukee Brewers in Game 5 of the NLDS and, with both League Championship Series underway, the offseason will be here before we know it.

After making a nine-game improvement over 2024, it'll be all eyes on Jed Hoyer and the Cubs' front office to see what moves they make. The departure of Kyle Tucker feels like a foregone conclusion, and any high-dollar, long-term play with Pete Alonso and Alex Bregman also seems unlikely. That said, there's a chance Chicago re-visits some trade talks for a front-line starter from this summer, and how the front office goes about replacing Tucker will be a major storyline.

With all that in mind, here are some important offseason dates every Cubs fan should know.

Important dates for Cubs fans to know in the 2025-26 MLB offseason

Qualifying offer deadline (five days after the World Series ends)

Depending on how the 2025 World Series plays out, the qualifying offer deadline will fall somewhere between Nov. 2 and Nov. 6. Five days after the Fall Classic concludes, teams must determine whether or not to extend qualifying offers to free agents.

The Cubs will, without a doubt, make Kyle Tucker a qualifying offer, which is projected to be around $22 million this offseason. The four-time All-Star will hit the open market searching for a major payday and Chicago isn't expected to push their chips in at the $300-400 million price range.

Shota Imanaga could be another qualifying offer candidate, depending on how his intricately bizarre contract situation plays out. The left-hander's rocky second half and subpar postseason showing, paired with a looming lockout in 2026, complicates what once looked like a no-brainer decision for Hoyer.

Non-tender deadline (Nov. 21)

This year's non-tender deadline falls on Nov. 21, right on the heels of the Owners Meetings in New York City (11/18-11/20). The Cubs' main non-tender candidate is right-hander Eli Morgan, a trade pick-up from Cleveland last year who made just seven appearances and did not appear in a game after mid-April. There could be other non-tenders, of course, but that's one that immediately comes to mind.

MLB Winter Meetings (December 8-11)

This year's Winter Meetings take place from Dec. 8-11 in Orlando. We always hope for major blockbusters to come together with executives from all 30 MLB teams together in one place, but each year is different. The 2025 MLB Draft Lottery also takes place during the Winter Meetings, set for Dec. 9 at 4 pm ET. The 2025 MLB Rule 5 Draft takes place on Dec. 10 from 2-4p ET.

2026 Cubs Convention (January 16-18)

The 2026 Cubs Convention is expected to be the kickoff of a year-long celebration of the 2016 team. Obviously, next year marks the 10-year anniversary of that curse-breaking club and with Anthony Rizzo back in the organization as an ambassador, we could see a lot of familiar faces from that club at the Sheraton in mid-January.

Pitchers and catchers report to spring training (February 2025)

At last. In February, pitchers and catchers will report to the Cubs' spring training complex in Mesa, Arizona to get to work in preparation of the 2026 MLB season. Chicago's Cactus League schedule has not yet been announced, but should be released sometime this fall.