The offseason is officially here.

The Los Angeles Dodgers became the first team since the 1998-2000 Yankees to repeat as World Series champions. The Yankees, following an exit in the American League Division Series at the hands of the runner-up Toronto Blue Jays, have work to do this winter to improve their roster.

Some of their biggest needs include filling two outfield vacancies, upgrading the bullpen, finding a platoon option at third base and first base, and getting at least one more starting pitcher.

To set the stage for the Yankees’ offseason agenda, here’s a look at the key dates in the coming weeks and months and how they affect the club.

Nov. 2: First day after the World Series

Paul Blackburn, Paul Goldschmidt, Trent Grisham, Amed Rosario, Austin Slater, Luke Weaver, Devin Williams and Ryan Yarbrough all officially became free agents on Sunday. The Yankees have a five-day window to exclusively negotiate with them. It’s rare for deals to get done during this time.

Trades are also permitted now that the World Series has ended.

Nov. 6: Fifth day after the World Series

With Cody Bellinger opting out of his player option, the Yankees must decide whether to re-sign him to a long-term deal in free agency. (Cole Burston / Getty Images)

This is the first important deadline for the Yankees this offseason. It’s the day when clubs and players must make their decisions on options, reinstate all players on the 60-day injured list and the deadline to tender qualifying offers (5 p.m. ET). Major-league free agents are free to sign with any club as of 5 p.m. ET on Thursday.

The Yankees have three players who have options: Cody Bellinger, Tim Hill and Jonathan Loáisiga. Bellinger will opt out of his $25 million player option to seek a long-term contract in free agency. The Yankees will likely exercise their $3 million club option to retain Hill, a left-handed specialist. Loáisiga will likely enter free agency after another injury-riddled season, as the club is expected to decline a $5 million option for the right-handed reliever.

The Yankees had four players finish the season on the 60-day injured list: Oswaldo Cabrera, Gerrit Cole, Jake Cousins and Clarke Schmidt. When they are reinstated, they will officially be back on the 40-man roster.

The decision with the most intrigue for this deadline is whether the Yankees will give Trent Grisham the one-year, $22.025 million qualifying offer. Bellinger is ineligible to receive the QO because the Chicago Cubs gave him one in 2024, which he rejected. Devin Williams and Luke Weaver technically could receive the QO, but they are considered long-shot candidates.

If the Yankees give Grisham the qualifying offer, he’ll have until Nov. 18 to accept or reject it. If the Yankees extend him the QO and he rejects it, the two sides could still agree to a long-term contract. If Grisham were to sign with another team after receiving the QO, the Yankees would receive a compensatory 2026 draft pick after the fourth round is completed.

Grisham is coming off a career season with 34 home runs and a 129 wRC+. Contact quality metrics suggest that his offensive breakout wasn’t a fluke. His barrel percentage, wOBA and xwOBA were all career-bests. Combining his ability to hit the ball hard with a career-high pull air percentage, Grisham benefited greatly from playing half of his games at Yankee Stadium.

Center field is one of the weaker positions in the sport, especially offensively. Grisham’s defense was overrated by Yankees manager Aaron Boone, who raved about his ability to man the center of the outfield. However, only five center fielders were worse in outs above average this season. Grisham’s athleticism has sharply declined over the past few seasons. If that trend continues, Grisham, who turned 29 on Saturday, will be a corner outfielder sooner rather than later.

With the Yankees likely pursuing Bellinger with a long-term deal, it’s unlikely they’d also pursue Grisham in free agency. It’s possible the only way Grisham returns is if he signs the qualifying offer, but it isn’t a given that he’ll receive one.

Nov. 10-13: General managers meetings

The purpose of GM meetings is for teams to come together and gather more intel on what their competitors are looking for in the offseason. It’s where initial trade talks usually begin, free agents are discussed and team needs become clearer.

This year’s meetings are in Las Vegas. Brian Cashman and the other AL GMs will speak with reporters on Nov. 12.

Nov. 13: MVP announced

Aaron Judge will win his third MVP award if the voters choose him over Cal Raleigh. (Steph Chambers / Getty Images)

Aaron Judge could become the fourth Yankee to win at least three MVPs, joining Mickey Mantle, Yogi Berra and Joe DiMaggio. Judge’s main competition this season was Seattle Mariners catcher Cal Raleigh, who hit 60 home runs and helped Seattle win its first American League West title since 2001.

The key stats for Judge and Raleigh aren’t particularly close; the Yankees’ right fielder should win. He leads Raleigh in all of the important statistics such as OPS, fWAR and wRC+. Judge also won his first batting title this season.

Voters could opt for Raleigh, who became the first catcher to hit at least 60 home runs in a single season. But if they emphasize the all-encompassing stats, Judge should win.

Nov. 18: Major-league and minor-league reserve lists due

By 6 p.m. ET on Nov. 18, teams must add players to their 40-man rosters to protect them from the Rule 5 draft in December. Players who signed at 18 years old or younger must be added to the 40-man roster within five seasons to be protected from that draft. Players who signed at 19 or older have to be added within four years.

Here are the notable Yankees prospects who are Rule 5 eligible this year: C Manuel Palencia, 1B T.J. Rumfield, OF Jace Avina, OF Spencer Jones, SP Elmer Rodriguez-Cruz, SP Brendan Beck, SP Chase Hampton, SP Brock Selvidge, SP Allen Facundo, SP Henry Lalane, RP Eric Reyzelman and RP Harrison Cohen.

The only two locks to be protected are Jones and Rodriguez-Cruz, both of whom are top 10 prospects. Depending on what the Yankees do this offseason, Jones could be in the mix to start in center field for the Yankees in 2026. Rodriguez-Cruz was acquired by New York in the trade that sent Carlos Narváez to Boston last December. The right-hander could be in the majors as soon as next year.

Teams that select a player in the Rule 5 draft must pay $100,000 to the club from which the player was selected. The player also must remain on the new club’s 26-man roster for the entire season or else they will be placed on waivers. If the player is not claimed, he must be offered back to his original team for $50,000.

Nov. 21: Tender deadline

Mark Leiter Jr. is among the club’s non-tender candidates. (Michael Reaves / Getty Images)

The Yankees have 14 arbitration-eligible players. The majority of those players will get tendered a contract. If a team decides to non-tender a player, he becomes an unrestricted free agent and is immediately removed from the 40-man roster.

Here are the 14 players who are eligible for arbitration, along with their projected salaries, according to MLB Trade Rumors:

• Jazz Chisholm Jr. (ARB 3, $10.2 million)
• David Bednar (ARB 3, $9 million)
• Clarke Schmidt (ARB 3, $4.9 million)
• Mark Leiter Jr. (ARB 3, $3 million)
• Camilo Doval (ARB 2, $6.6 million)
• Scott Effross (ARB 2, $800,000)
• Anthony Volpe (ARB 1, $3.9 million)
• Luis Gil (ARB 1, $2.1 million)
• José Caballero (ARB 1, $1.9 million)
• Fernando Cruz (ARB 1, $1.3 million)
• Oswaldo Cabrera (ARB 1, $1.2 million)
• Jake Bird (ARB 1, $1 million)
• Ian Hamilton (ARB 1, $941,000)
• Jake Cousins (ARB 1, $841,000)

Leiter, Effross, Hamilton and Cousins are non-tender candidates. Leiter was ineffective this season, and the Yankees probably could upgrade his spot in the bullpen for a similar salary in free agency. Effross has not been able to bounce back well enough after two major injuries. Hamilton lost his command this year and was eventually demoted to the minor leagues. Cousins will likely miss the entire 2026 season after undergoing Tommy John surgery in the middle of the summer.

Dec. 8-11: Winter Meetings

A significant number of signings and trades take place at the Winter Meetings, as the sport convenes for what is, essentially, a massive networking event. This year’s event will be held in Orlando. Last year, the Yankees found out Juan Soto was signing with the New York Mets on the first day of the Winter Meetings. The club then quickly pivoted to beefing up its run prevention by inking Max Fried to an eight-year contract. This year, top free agents such as Kyle Tucker and Cody Bellinger could be signed by the end of the meetings.

The Rule 5 draft will be held on Dec. 10. The Yankees have not made a MLB selection in the Rule 5 draft since 2011 (Brad Meyers).

Jan. 8: Deadline to agree to contract with players eligible for arbitration

This is the final date for teams and arbitration-eligible players to agree on one-year contracts. If teams and players cannot reach an agreement by then, the two sides will exchange dollar figures and schedule a date for arbitration in February.

Last offseason, Leiter became the first Yankee to go to arbitration since 2017. Leiter lost to the Yankees after asking for $2.5 million; he made $2.05 million in salary this year. Before Leiter, Dellin Betances was the last Yankee to go to arbitration. The club was very close to going to arbitration with Judge in 2022 before agreeing to a $19 million contract.

Mid-February: Pitchers and catchers report

MLB hasn’t released the dates when pitchers and catchers will report, but it should be sometime during the week of Feb. 9.