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2020-2021 Offseason Calendar

Here are the dates to know for the winter ahead.

Philadelphia Phillies v Washington Nationals Photo by G Fiume/Getty Images

The offseason is officially here, and there is a lot of work for the Red Sox to do. There’s obviously no baseball over the next few months, but there is still a lot that needs to happen for every team around the league, even in an offseason that almost certainly is going to be rough for those of us who would like to see action. Following a shortened season without fans, it seems likely financial talk will take center stage yet again this winter.

We’ll cross that bridge when we get to it, though. In the meantime, there are a lot of dates to keep track of this time of year and it can be annoying to have to Google for each specific one. So, I find it easier to just put them all in one place, and we’ll keep this pinned on the front page for reference purposes throughout the winter. A hat tip to Anthony Castrovince over at for some of these dates as well.

Players file for Free Agency: October 28

That’s today! Players can officially file for free agency at 9:00 AM the day after the World Series ends. For the Red Sox, Jackie Bradley Jr. is the only player for whom this applies. This is followed by a quiet period of five days, however, where players such as Bradley can only sign back with their own team. They are free to sign deals with new days five days after the conclusion of the season, which this year would be November 1.

Option Deadline/Start of Free Agency/Qualifying Offer Deadline: November 1

As I just mentioned above, free agents can start signing with other teams five days after the World Series ends. That is also the day options must be decided for players. For the Red Sox, that means they must make a decision on Martín Pérez’s option by this date and J.D. Martinez must make a decision on his opt-out by this date as well. On top of all that, teams have until this date to extend qualifying offer to free agents. The Red Sox almost certainly won’t extend one to Bradley.

Gold Glove Award Winners are Announced: November 3

The Red Sox had no finalists for the award at any position.

Rookies of the Year Announced: November 9

The best Red Sox rookies this year were Bobby Dalbec and Tanner Houck, neither of which played enough to get real consideration for this award.

Managers of the Year Announced: November 10

I will go out on a limb and say Ron Roenicke will not get consideration here.

Deadline for Players to Accept or Decline Qualifying Offer: November 11

Players have until ten days after they receive a qualifying offer to decide whether or not they will accept it. That means the latest they can do so will be on the 11th. As I said, no Red Sox players are likely to get the offer, but they could potentially be looking to target players that would be on this list.

Cy Youngs Announced: November 11

Again, no Red Sox players will be in consideration.

MVPs Announced: November 12

There will be no Red Sox winner here, but the ballot is large enough that it’s not inconceivable that Xander Bogaerts and/or Alex Verdugo get some down-ballot votes.

Rule 5 Protection Deadline: November 20

Teams have until this date to add players not currently on the 40-man roster in order to protect them from being selected in the Rule 5 Draft. As things stand now, Boston has six players who are obvious protection candidates in Jay Groome, Bryan Mata, Hudson Potts, Jeisson Rosario, Connor Seabold, and Connor Wong. There are also fringe candidates like Eduard Bazardo and Pedro Castellanos, though they likely won’t extend much beyond the six obvious ones.

Non-Tender Deadline: December 2

Teams have until this date to tender contracts to players who are not already signed to guaranteed deals. Among arbitration-eligible players, the non-tender candidates for the Red Sox are José Peraza, Dylan Covey, Ryan Weber and Austin Brice.

Winter Meetings: December 6-December 10

It seems unlikely there will be formal Winter Meetings this year, though as of now this is what’s on the table. It’s possible they move it to a virtual format, though I’m not even entirely sure what that would look like.

Rule 5 Draft: December 10

All eligible players not protected by November 20 are eligible to be taken in this draft. If selected, the player must remain on the active roster for the entirety of the following season or their original team can take them back. The Red Sox successfully kept Jonathan Araúz on the roster for all of 2020. There are enough holes to fill this year that the Red Sox could take another player in this winter’s draft, though that would only add to their 40-man roster crunch.

Arbitration Figures Exchanged: January 15

Teams must exchange arbitration figures with players to whom they tendered a contract by this date. In the past, this was a key date for negotiations with players and teams often meeting in the middle. More recently, though, more teams have gone with the file-and-trial method which means once this date comes they just go to an arbitration hearing no matter what. Those hearings take place in February and after hearing arguments arbiters must pick one side’s proposed 2021 salary. There could be even more hearings than usual this year as normal precedent may come into question given the shortened season.

Hall of Fame Class Announcement: January ?

There is no official date for this as far as I can tell at this point, so I’ll update once that comes out. Last year it was on January 21. Curt Schilling may be the lone player inducted this year after getting 70 percent of the vote last year. The notable first timers on this ballot will be Mark Buehrle, Tim Hudson and Torii Hunter.

Pitchers and Catchers Report: February 16(?)

Most teams have not yet announced when pitchers and catchers will report, but the Orioles have their date set at February 16 so presumably the Red Sox will also be in camp at some point around there. Of course, that is all dependent on how things progress with COVID in this country, which is anybody’s guess.

Northeastern Game: February 26

The annual spring training opener against Northeastern is February 26, again pending COVID.

Opening Day: April 1

The Red Sox open up their 2021 regular season at home against the Orioles.