| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (0) Wakefield Warriors at (3) Winchester Red & Black | O'Brien Arena |
| Jan. 2 Postponed | Reading Rockets at Winchester Red & Black | O'Brien Arena |
| January 05, 2021 | (3) Winchester Red & Black at (0) Wakefield Warriors | Stoneham Arena |
| Jan. 6 Postponed | Winchester Red & Black at Reading Rockets
make up date TBA |
Burbank Ice Arena |
| January 13, 2021 | (2) Belmont Marauders at (0) Winchester Red & Black | O'Brien Arena |
| Jan. 13 Postponed | Reading Rockets at Winchester Red & Black | O'Brien Arena |
| January 18, 2021 | (2) Winchester Red & Black at (2) Belmont Marauders | Skip Viglirolo Rink |
| January 20, 2021 | (5) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
| January 27, 2021 | (2) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| Feb. 4 Postponed | Winchester Red & Black at Lexington Minutemen | O'Brien Arena |
| February 10, 2021 | (2) Lexington Minutemen at (4) Winchester Red & Black | O'Brien Arena |
| February 13, 2021 | (3) Winchester Red & Black at (4) Woburn Tanners | O'Brien Arena |
| February 15, 2021 | (1) Woburn Tanners at (3) Winchester Red & Black | O'Brien Arena |
| February 17, 2021 | (5) Winchester Red & Black at (1) Melrose Red Hawks
Middlesex League tournament |
Stoneham Arena |
| February 18, 2021 | (0) Burlington Red Devils at (4) Winchester Red & Black | O'Brien Arena |
| February 20, 2021 | (1) Winchester Red & Black at (3) Reading Rockets | O'Brien Arena |
