MLB Offseason 2026 Key Dates: Free Agency Start, Awards Schedule, Winter Meetings and CBA Expiration

Major League Baseball (MLB) free agency opens the day after the World Series ends, which is Wednesday, Oct. 28 to Sunday, Nov. 1, 2026 depending on the final game, according to MLB.com’s offseason rules guide. MLB.com’s awards guide (Oct. 26, 2026) then lists the Gold Glove Awards on Sunday, Nov. 1 through the Silver Slugger Awards on Tuesday, Nov. 17. Milwaukee leads Tampa Bay 3-0 in the World Series, and Game 4 is Tuesday, Oct. 27 at 8 p.m. Eastern Time (ET). We do not predict how it ends, so the table below covers every possible final game. The details are in our 2026 World Series schedule.

When does free agency start, by the day the World Series ends?

MLB.com’s guide says: “Officially, players become free agents the day after the conclusion of the World Series.” Teams must make qualifying offers “within five days of the conclusion of the World Series,” and players “cannot sign with a new team until 5 p.m. ET on the fifth day after the conclusion of the World Series.” That guide is from Oct. 23, 2025. We applied its rules to this year’s possible final games and counted the weekdays ourselves.

If the Series ends in	Final game	Players become free agents	Qualifying offer deadline (five days after)	Free agents can sign with new clubs
Game 4	Tue., Oct. 27	Wed., Oct. 28	Sun., Nov. 1	Sun., Nov. 1, 5 p.m. ET
Game 5	Wed., Oct. 28	Thu., Oct. 29	Mon., Nov. 2	Mon., Nov. 2, 5 p.m. ET
Game 6	Fri., Oct. 30	Sat., Oct. 31	Wed., Nov. 4	Wed., Nov. 4, 5 p.m. ET
Game 7	Sat., Oct. 31	Sun., Nov. 1	Thu., Nov. 5	Thu., Nov. 5, 5 p.m. ET

The game dates come from the MLB Stats application programming interface (API) schedule. Games 5 to 7 are played only if needed. The qualifying offer column is our count of the five-day window; MLB has not yet announced the 2026 deadline.

What is the 2026 qualifying offer?

Not yet announced. MLB.com (Aug. 8, 2026) says the offer is “set at the average salary of MLB’s top 125 highest-paid players (worth $22.025 million last offseason).” In 2025, players had until 4 p.m. ET on Nov. 18 to accept. The 2026 accept deadline is not yet announced either.

When are the 2026 MLB awards announced?

Every date below is from MLB.com’s awards guide of Oct. 26, 2026. The Baseball Writers’ Association of America (BBWAA) votes on four of them.

Date	Award
Sun., Nov. 1	Rawlings Gold Glove Awards, 8:30 p.m. ET on ESPN
Fri., Nov. 6	Platinum Glove Awards; Heart & Hustle Awards
Mon., Nov. 9	BBWAA Rookie of the Year
Tue., Nov. 10	BBWAA Manager of the Year
Wed., Nov. 11	BBWAA Cy Young; BBWAA Relief Pitcher of the Year; All-MLB Teams; Hank Aaron Awards; Comeback Player of the Year; Rivera/Hoffman Reliever of the Year; Edgar Martinez Outstanding Designated Hitter
Thu., Nov. 12	BBWAA M.V.P. Awards
Tue., Nov. 17	Silver Slugger Awards

This is the first season the BBWAA gives a Relief Pitcher of the Year award. Several of the Nov. 11 honors are announced in a show that begins at 9 p.m. ET. The Executive of the Year award is announced during the General Manager (GM) Meetings in Las Vegas. Show times for the other days are not yet announced.

What are all the MLB offseason key dates from Oct. 27, 2026 to Opening Day 2027?

Each row is labeled official (MLB or MLB.com), reported (a news outlet, not MLB) or a 2025 value (last year’s date, not this year’s).

Date	Event	Label
Tue., Oct. 27, 2026	World Series Game 4, 8 p.m. ET	Official (MLB schedule)
Wed., Oct. 28 to Sat., Oct. 31	Games 5, 6 and 7 if needed (Oct. 28, 30 and 31)	Official (MLB schedule)
Day after the final game	Players become free agents (Oct. 28 to Nov. 1)	Official rule
Five days after the final game	Qualifying offer deadline and first day to sign, 5 p.m. ET (Nov. 1 to Nov. 5)	Official rule; 2026 dates not yet announced
Sun., Nov. 1	Gold Glove Awards, 8:30 p.m. ET, ESPN	Official
Fri., Nov. 6	Platinum Glove and Heart & Hustle Awards	Official
Mon., Nov. 9 to Thu., Nov. 12	GM Meetings, Las Vegas	Reported (Just Baseball); MLB.com confirms Las Vegas only
Mon., Nov. 9 to Thu., Nov. 12	Rookie of the Year, Manager of the Year, Cy Young, M.V.P.	Official
Tue., Nov. 17	Silver Slugger Awards	Official
Wed., Nov. 18, 4 p.m. ET	Last year’s qualifying offer accept deadline	2025 value
Fri., Nov. 20, 2026	Non-tender deadline	Reported (Just Baseball); the 2025 deadline was Nov. 21
Tue., Dec. 1, 2026, 11:59 p.m. ET	Collective Bargaining Agreement (CBA) expires	Reported (Just Baseball)
Mon., Dec. 7 to Wed., Dec. 9	Winter Meetings, San Diego, “currently scheduled”	Reported (Just Baseball)
Fri., Feb. 19, 2027	Spring Training games begin	Official (MLB, Sept. 4, 2026)
Wed., Mar. 24, 2027	Opening Night on Netflix	Official (MLB, Sept. 4, 2026)
Thu., Mar. 25, 2027	Opening Day, 14 games	Official (MLB, Sept. 4, 2026)

What happens when the CBA expires on Dec. 1?

Just Baseball (Oct. 13, 2026) reports the Collective Bargaining Agreement “will expire on December 1, 2026 at 11:59 p.m. ET.” The Associated Press reported the same expiration when the deal was signed in 2022. MLB and the MLB Players Association have not published a 2026 calendar of these dates, so the Winter Meetings and non-tender dates above should be rechecked. We do not speculate beyond that: the current agreement expires on that date.

What has MLB not announced yet?

The 2026 qualifying offer amount and accept deadline, the Rule 5 Draft date, the date the BBWAA names its finalists, award show times beyond those above and the 2027 salary arbitration exchange date are all not yet announced in the sources we used. We will update this story when they appear.

Free MLB offseason dates printable

Our one-page list puts free agency, the awards, the meetings, the CBA expiration and Opening Day in date order. Mark the dates on the November 2026 printable calendar and the December 2026 printable calendar, then count down on the March 2027 printable calendar. For the end of the season, see MLB Opening Day 2027, and for another sport’s dates, our printable National Football League (NFL) schedule.