| Date & Time | Game | Venue |
|---|---|---|
| Jan. 2 Postponed | Winchester Red & Black at Reading Rockets | Burbank Ice Arena |
| Jan. 6 Postponed | Reading Rockets at Winchester Red & Black
make up date TBA |
O'Brien Arena |
| January 13, 2021 | (2) Winchester Red & Black at (2) Belmont Marauders | Skip Viglirolo Rink |
| January 18, 2021 | (3) Belmont Marauders at (2) Winchester Red & Black | O'Brien Arena |
| January 20, 2021 | (3) Arlington Spy Ponders at (2) Winchester Red & Black | O'Brien Arena |
| Jan. 27 Postponed | Winchester Red & Black at Arlington Spy Ponders | Ed Burns Arena |
| February 04, 2021 | (2) Lexington Minutemen at (6) Winchester Red & Black | O'Brien Arena |
| February 06, 2021 | (2) Winchester Red & Black at (4) Arlington Spy Ponders | Ed Burns Arena |
| February 11, 2021 | (4) Winchester Red & Black at (0) Lexington Minutemen | O'Brien Arena |
| February 13, 2021 | (6) Woburn Tanners at (3) Winchester Red & Black | O'Brien Arena |
| February 15, 2021 | (0) Winchester Red & Black at (0) Woburn Tanners | O'Brien Arena |
| February 17, 2021 | (3) Winchester Red & Black at (0) Belmont Marauders
Middlesex League tournament |
Burlington Ice Palace |
| February 18, 2021 | (1) Winchester Red & Black at (2) Arlington Spy Ponders | Ed Burns Arena |
