| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (5) Weymouth Wildcats at (3) Wellesley Raiders | Wellesley Sports Center |
| Jan. 13 Postponed | Newton North Tigers at Wellesley Raiders | Wellesley Sports Center |
| Jan. 16 Postponed | Wellesley Raiders at Newton North Tigers | John A. Ryan Arena |
| January 20, 2021 | (2) Wellesley Raiders at (4) Natick Red Hawks | Chase Arena |
| Jan. 20 Postponed | (1) Needham Rockets at (4) Wellesley Raiders | Wellesley Sports Center |
| January 23, 2021 | (2) Wellesley Raiders at (1) Natick Red Hawks | Babson Skating Center |
| January 27, 2021 | (1) Walpole Timberwolves at (0) Wellesley Raiders | Wellesley Sports Center |
| January 30, 2021 | (0) Wellesley Raiders at (5) Walpole Timberwolves | Rodman Arena |
| February 03, 2021 | (2) Wellesley Raiders at (0) Brookline Warriors | Walter Brown Arena |
| February 06, 2021 | (2) Brookline Warriors at (4) Wellesley Raiders | Wellesley Sports Center |
| February 10, 2021 | (2) Wellesley Raiders at (2) Brookline Warriors | Walter Brown Arena |
| February 13, 2021 | (2) Natick Red Hawks at (2) Wellesley Raiders | Wellesley Sports Center |
