| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (0) Wakefield Warriors at (3) Winchester Red & Black | O'Brien Arena |
| January 05, 2021 | (3) Winchester Red & Black at (0) Wakefield Warriors | Stoneham Arena |
| January 10, 2021 | (3) Wilmington Wildcats at (3) Wakefield Warriors | Stoneham Arena |
| January 15, 2021 | (2) Wakefield Warriors at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 18, 2021 | (1) Wakefield Warriors at (3) Arlington Spy Ponders | Ristuccia Memorial Arena |
| January 20, 2021 | (1) Burlington Red Devils at (3) Wakefield Warriors | Stoneham Arena |
| January 27, 2021 | (2) Wakefield Warriors at (1) Burlington Red Devils | Burlington Ice Palace |
| February 02, 2021 | (2) Watertown/Wayland Raiders at (7) Wakefield Warriors
Make-up TBD |
John A. Ryan Arena |
| February 06, 2021 | (2) Wakefield Warriors at (3) Stoneham Spartans | Stoneham Arena |
| February 11, 2021 | (2) Stoneham Spartans at (1) Wakefield Warriors | Stoneham Arena |
| February 13, 2021 | (3) Wakefield Warriors at (4) Melrose Red Hawks | Stoneham Arena |
| February 15, 2021 | (6) Melrose Red Hawks at (0) Wakefield Warriors | Stoneham Arena |
| February 17, 2021 | (1) Wakefield Warriors at (2) Belmont Marauders
Middlesex league tournament |
John A. Ryan Arena |
