| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2021 | (2) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| December 18, 2021 | (4) Winchester Red & Black at (2) Wilmington Wildcats | Ristuccia Memorial Arena |
| December 21, 2021 | (1) Stoneham Spartans at (3) Winchester Red & Black | O'Brien Arena |
| Dec. 31 (Time TBA) | (2) Winchester Red & Black at (0) Reading Rockets | Burbank Ice Arena |
| January 05, 2022 | (0) Winchester Red & Black at (6) Belmont Marauders | Skip Viglirolo Rink |
| January 08, 2022 | (6) Arlington Spy Ponders at (0) Winchester Red & Black | John A. Ryan Arena |
| January 12, 2022 | (1) Woburn Tanners at (2) Winchester Red & Black | O'Brien Arena |
| January 17, 2022 | (5) Winchester Red & Black at (1) Melrose Red Hawks | Stoneham Arena |
| January 20, 2022 | (1) BC High Eagles at (2) Winchester Red & Black | O'Brien Arena |
| January 22, 2022 | (1) Wakefield Warriors at (2) Winchester Red & Black | O'Brien Arena |
| January 24, 2022 | (2) Watertown/Wayland Raiders at (2) Winchester Red & Black | O'Brien Arena |
| January 26, 2022 | (3) Winchester Red & Black at (3) St. Mary's Lynn Spartans | Connery Memorial Arena |
| January 28, 2022 | (1) Reading Rockets at (4) Winchester Red & Black | O'Brien Arena |
| January 30, 2022 | (1) Winchester Red & Black at (2) Hingham Harbormen
Ed Burns Showcase Quarterfinals |
Ed Burns Arena |
| February 02, 2022 | (3) Belmont Marauders at (2) Winchester Red & Black | O'Brien Arena |
| February 06, 2022 | (0) Winchester Red & Black at (6) Braintree Wamps
Ed Burns Showcase Semifinal Round - Olympic Rink |
Rodman Arena |
| February 09, 2022 | (3) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| Feb. 12 Postponed | Winchester Red & Black at Arlington Catholic Cougars | Breakaway Ice Center |
| February 12, 2022 | (0) Winchester Red & Black at (4) Austin Prep Cougars | Breakaway Ice Center |
| February 13, 2022 | (0) Weymouth Wildcats at (5) Winchester Red & Black
Ed Burns Coffee Pot final round game - Red Rink |
Canton Ice House |
| February 16, 2022 | (3) Winchester Red & Black at (4) Hingham Harbormen | Pilgrim Arena |
| February 20, 2022 | (3) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
| March 03, 2022 | (1) Central Catholic Raiders at (2) Winchester Red & Black
Boys Division 1 Tournament |
O'Brien Arena |
| March 07, 2022 | (0) Winchester Red & Black at (7) St. John's Prep Eagles
Boys Division 1 Tournament |
Essex Sports Center |
