Jan. 31, 2021–Feb. 9, 2021 — 2021 CFL Pending Free Agent Negotiation Window

Feb. 9, 2021 12:00 PM EST — 2021 CFL Free Agency period begins

April 15, 2021 1:00 PM EDT — 2021 CFL Global Draft

May 4, 2021 7:00 PM EDT — 2021 CFL Amateur Draft

July 19, 2021 10:00 PM EDT — Rosters limited to 75 standard player contracts excluding non-counters

July 30, 2021 10:00 PM EDT — Final Cut-down date to regular season roster size

Aug. 5, 2021 8:30 PM EDT — 2021 CFL Regular Season kicks off

Sept. 3–6, 2021 — 2021 Labour Day Weekend Games

Oct. 11, 2021 — 2021 Thanksgiving Day Games

Nov. 28, 2021 — Division Semi-Finals

Dec. 5, 2021 — Division Finals

Dec. 12, 2021 6:00 PM EST — 108th Grey Cup at Tim Hortons Field, Hamilton, ON