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MLB Offseason Dates: Key Dates for 2021-22 MLB Offseason Including Awards, Free Agency, CBA, Winter Meetings & More

Adam Taylor McKillop
MLB Offseason dates: key dates for the 2021-22 MLB Offseason including awards, free agency, Winter Meetings and CBA expiration.
MLB Offseason dates: key dates for the 2021-22 MLB Offseason including awards, free agency, Winter Meetings and CBA expiration. / John Fisher/GettyImages
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Whlie the Atlanta Braves are still buzzing from their 2021 World Series Title the rest of the MLB's 29 teams are looking toward the 2022 campaign, including some key dates for the offseason schedule.

Award season already kicked off and the league named its 2021 Gold Glove award winners on Sunday, Nov. 7.

MLB Offseason Awards

Here's a full breakdown for the remaining MLB regular season awards, including MVP, Rookie of the Year, Manager of the Year, Cy Young and Comeback Player of the Year.

- Monday, Nov. 15: Rookie of the Year
- Tuesday, Nov. 16: Manager of the Year
- Wednesday, Nov. 17: Cy Young
- Thursday, Nov. 18: MVP
- Monday, Nov. 22: Comeback Player of the Year

MLB Free Agency and Qualifying Offers

November 7 marked the beginning of MLB Free Agency, a process that starts with qualifying offers. MLB teams must choose to extend nor not to extend qualifying offers to eligible players on this date. Free Agency officially begins as players are now allowed to negotiate and sign with any team outside of their 2021 ball clubs.

MLB Winter Meetings

The MLB holds two sets of important Winter meetings: the GM meetings in November and the official Winter Meetings in December.

The GM Meetings are scheduled for Nov. 9-11 as all 30 MLB general managers meet to discuss off-the-field matters.

MLB's official Winter Meetings are set to take place from Dec. 6-9. These dates usually mark the busiest time of the offseason and the best opportunity for teams to land major free-agent acquisitions or trades.

Collective Bargaining Agreement (CBA) Expiration

The expiration of the MLB's current CBA is arguably the most important date of the offseason. Major League Baseball's current CBA expires at 11:59 p.m. ET on Dec. 1. The league and MLB Players Association must come to terms on a new CBA by this date or the rest of the offseason and 2022 regular season are put in jeopardy.

The potential fallout of both sides not reaching an agreement includes a potential work stoppage or the delay of the 2022 season. Reports currently suggest both sides have not made substantial progress on a new agreement.


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Adam Taylor McKillop is not a FanDuel employee. In addition to providing DFS gameplay advice, Adam Taylor also participates in DFS contests on FanDuel using his personal account, username atmckillop. While the strategies and player selections recommended in his articles are his personal views, he may deploy different strategies and player selections when entering contests with his personal account. The views expressed in their articles are the author's alone and do not necessarily reflect the views of FanDuel. 

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