This should be a busy offseason for the Arizona Diamondbacks to build a competitive roster after a fourth-place finish, and it officially starts the day after the World Series wraps up.

Major League Baseball’s offseason can be a slow burn, but there are many checkpoints that start immediately after the Fall Classic, with free agents able to negotiate with their own teams and the trade market officially opening up.

With the World Series between the Los Angeles Dodgers and Toronto Blue Jays plowing ahead, let’s mark down the key days on the offseason calendar (we’ll stick to awards that are relevant to Arizona):

Diamondbacks offseason dates to watch

1 day after World Series – Players become free agents

Teams can begin negotiating with their own free agents starting one day after the World Series.

Arizona’s key free agents are starter Zac Gallen, reliever Jalen Beeks and catcher James McCann. This is also when major league trades can officially start happening.

5 days after World Series – Free agency starts, qualifying offer deadline, roster cleaning up

After the initial five-day period passes, free agents can start negotiating with any team.

Teams must extend qualifying offers to free agents by this time, as well, which is a $22.03 million deal for one season. Gallen is likely to receive this offer from the Diamondbacks.

Additionally, players and clubs will have to decide on options. Diamondbacks left fielder Lourdes Gurriel Jr. has a $13 million player option for 2026, which he is incentivized to pick up considering he tore his ACL in September and will miss most of next season.

Teams also have to remove players from the 60-day injured list and reinsert them onto the 40-man roster.

Arizona has nine players on the 60-day IL without nine open spots. They have five more players than openings, meaning a series of waivers is coming. All-in-all, the free agent market will be cleared up at this point.

Nov. 2 – Gold Glove winners announced

Right fielder Corbin Carroll is Arizona’s lone Gold Glove finalist.

He is competing with San Diego’s Fernando Tatis Jr. and Milwaukee’s Sal Frelick for the award that honors the best defender at each position in each league.

Nov. 6 – National League Silver Slugger awards announced

Carroll, shortstop Geraldo Perdomo and second baseman Ketel Marte are finalists for a Silver Slugger, which is an award for the best offensive player at each position in each league.

Your 2025 National League @SluggerNation Silver Slugger Award finalists 💪

NL winners will be announced on Thursday, Nov. 6. American League finalists will be announced tomorrow, with AL winners on Friday, Nov. 7. pic.twitter.com/LppycGSfiu

— MLB (@MLB) October 22, 2025

Nov. 9 – Fall Stars Game

Baseball games do not stop after the World Series. The Arizona Fall League provides opportunities for prospects through the middle of November, while winter leagues in other countries, such as the Dominican Republic, Mexico and Venezuela, are underway.

The Fall Stars Game provides an opportunity here in Arizona for fans to see the best players from the AFL. The event is at Sloan Park.

Prospects Tommy Troy, LuJames Groover and Kristian Robinson represented the Diamondbacks in 2024.

The AFL title game is on Nov. 15 at Salt River Fields.

Nov. 11-13 – General managers meetings take place in Las Vegas

The GM meetings are where many offseason deals are born. Not a ton gets finalized here, but it is a critical step for trades and signings to come together and to preview the rest of the winter.

Nov. 13 – MVP, All-MLB teams announced

Shohei Ohtani will win the NL MVP, but Perdomo and Carroll should both finish top 10 in the race. Marte has an argument for down-ballot votes, as well.

All three Diamondbacks stars are in contention for the All-MLB teams. These honors, along with several others, will be revealed at the MLB Awards show in Las Vegas.

Nov. 18-20 – Owners meetings in New York City

With the threat of a lockout in 2027 after the collective bargaining agreement expires, there will be a lot to talk about here.

Nov. 18 – Qualifying offer decision deadline

Teams can gain draft compensation if their players decline the qualifying offer, while on the flip side, teams can surrender a draft pick by signing players who declined the offer from another team. The D-backs picked up a draft selection in 2025 with the departure of Christian Walker, but they also lost a pick since they signed Corbin Burnes.

Gallen is not expected to accept the QO.

Nov. 21 – Non-tender deadline

This is a big date for the Diamondbacks to potentially save money and open roster spots on the 40-man team. Clubs have to tender contracts to players with fewer than six years of service time and can decline to do so.

Dec. 8-11 – Winter meetings in Orlando

Hot stove watch will be underway at the annual meetings that bring teams together in the middle of the offseason to get things done. Offseason baseball conventions have gone on since the 1850s, and while modern communication somewhat lessens the importance of the winter meetings, they sometimes provide moments of drama.

The Red Sox traded for ace Garrett Crochet last year, while the Yankees signed Max Fried.

Dec. 9 – MLB Draft lottery

The meetings also provide a location for several key offseason points of business, like the draft lottery. The Diamondbacks did not expect to be in it, but here they are. Arizona has a 1.51% chance of winning the lottery, which is 10th-best.

The White Sox have the best odds at 27.7%.

Dec. 10 – Rule 5 Draft

Players who signed with their clubs at 18 or younger need to be on the 40-man roster within five years. Players who sign at 19 or older need to be on the 40-man roster within four years. If not, then they are subject to the Rule 5 Draft, which gives teams the opportunity to pry talent from another organization.

The catch is that players picked in the Rule 5 Draft must make the major league roster of the selecting team or else they can end up back where they started. Famously, the Diamondbacks lost future All-Star second baseman Dan Uggla to the Rule 5 Draft a couple of decades ago. Arizona has a long list of players in need of protection:

Notable #Dbacks prospects that are Rule 5 eligible:

Kohl Drake, Mitch Bratt, Dylan Ray, Spencer Giesting, Christian Cerda, Manuel Pena, Landon Sims, Gavin Conticello, Ivan Melendez, Alfred Morillo, and AJ Vukovich https://t.co/D8MyzLIqFP

— Diamondbacks Prospects 🐍 (@dbacksprospectz) October 17, 2025

Spring training will roll back around in February.

The World Baseball Classic returns next spring, starting up in March, so this offseason is a time to watch for national team roster news.

Team USA will take on Brazil to begin the group stage on March 6.