| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2021 | (3) Winchester Red & Black at (1) Burlington Red Devils | Burlington Ice Palace |
| December 21, 2021 | (0) Stoneham/Wilmington Spartans at (4) Winchester Red & Black | O'Brien Arena |
| December 28, 2021 | (6) Winchester Red & Black at (2) Lincoln-Sudbury Warriors | New England Sports Center |
| December 29, 2021 | (1) Canton Bulldogs at (5) Winchester Red & Black | O'Brien Arena |
| Dec. 31 Postponed | Winchester Red & Black at Reading Rockets
make-up TBA |
Burbank Ice Arena |
| January 12, 2022 | (4) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| January 15, 2022 | (1) Lexington Minutemen at (3) Winchester Red & Black | John A. Ryan Arena |
| January 17, 2022 | (9) Winchester Red & Black at (0) Melrose Red Hawks | Flynn Memorial Rink |
| January 22, 2022 | (0) Wakefield Warriors at (9) Winchester Red & Black | John A. Ryan Arena |
| January 24, 2022 | (0) Watertown Raiders at (3) Winchester Red & Black | John A. Ryan Arena |
| January 28, 2022 | (1) Reading Rockets at (4) Winchester Red & Black | O'Brien Arena |
| February 02, 2022 | (2) Belmont/Watertown Marauders at (2) Winchester Red & Black | John A. Ryan Arena |
| February 05, 2022 | (0) Winchester Red & Black at (3) Arlington Spy Ponders | Ed Burns Arena |
| February 09, 2022 | (0) Winchester Red & Black at (4) Woburn Tanners | O'Brien Arena |
| February 12, 2022 | (5) Winchester Red & Black at (1) Lexington Minutemen | Hayden Ice Facility |
| February 16, 2022 | (2) Winchester Red & Black at (2) Dennis-Yarmouth Dolphins | Tony Kent Arena |
| February 19, 2022 | (3) Winchester Red & Black at (0) Belmont/Watertown Marauders
re-scheduled from 1-5-22 |
Viglirolo - Belmont High School Skating Rink |
| February 22, 2022 | (2) Andover Golden Warriors at (2) Winchester Red & Black
Hingham Hockey Showcase |
Pilgrim Arena |
| February 24, 2022 | (2) Winchester Red & Black at (2) Acton-Boxboro Revolution
Hingham Tournament |
Pilgrim Arena |
| March 05, 2022 | (2) Wellesley Raiders at (4) Winchester Red & Black
Girls Division 2 Tournament |
O'Brien Arena |
| March 09, 2022 | (2) Winchester Red & Black at (0) Braintree Wamps
Girls Division 2 Tournament |
Zapustas Arena |
| March 12, 2022 | (1) Algonquin/Hudson Titans at (0) Winchester Red & Black
Girls Division 2 Tournament |
NorthStar Ice Sports |
