| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (0) Weymouth Wildcats at (7) Wellesley Raiders | Wellesley Sports Center |
| January 06, 2021 | (0) Wellesley Raiders at (5) Natick Red Hawks | Chase Arena |
| Jan. 9 Postponed | Wellesley Raiders at Framingham Flyers
make up date TBA |
Loring Arena |
| Jan. 13 Postponed | Wellesley Raiders at Newton North/South Tigers | John A. Ryan Arena |
| Jan. 16 Postponed | Newton North/South Tigers at Wellesley Raiders | Wellesley Sports Center |
| Jan. 20 Postponed | Wellesley Raiders at Needham Rockets | Babson Skating Center |
| Jan. 23 Postponed | Needham Rockets at Wellesley Raiders | Wellesley Sports Center |
| January 23, 2021 | (7) Natick Red Hawks at (5) Wellesley Raiders | Wellesley Sports Center |
| January 27, 2021 | (2) Wellesley Raiders at (1) Walpole Timberwolves | Rodman Arena |
| January 30, 2021 | (0) Walpole Timberwolves at (3) Wellesley Raiders | Wellesley Sports Center |
| February 03, 2021 | (0) Brookline Warriors at (8) Wellesley Raiders | Wellesley Sports Center |
| February 06, 2021 | (3) Wellesley Raiders at (1) Brookline Warriors | Murphy Memorial Rink |
| February 10, 2021 | (1) Brookline Warriors at (5) Wellesley Raiders | Wellesley Sports Center |
| February 13, 2021 | (2) Wellesley Raiders at (3) Natick Red Hawks | Chase Arena |
| February 14, 2021 | (1) Needham Rockets at (1) Wellesley Raiders | Wellesley Sports Center |
