| Date & Time | Game | Venue |
|---|---|---|
| January 09, 2021 | (4) Walpole Timberwolves at (4) Milton Wildcats | Ulin Memorial Rink |
| Jan. 13 Postponed | Walpole Timberwolves at Brookline Warriors | Rodman Arena |
| January 16, 2021 | (5) Needham Rockets at (2) Walpole Timberwolves | Babson Skating Center |
| Jan. 20 Postponed | Walpole Timberwolves at Weymouth Wildcats | Connell Memorial Rink |
| Jan. 23 Postponed | Weymouth Wildcats at Walpole Timberwolves | Rodman Arena |
| January 27, 2021 | (2) Wellesley/Lincoln-Sudbury Raiders at (1) Walpole Timberwolves | Rodman Arena |
| January 30, 2021 | (0) Walpole Timberwolves at (3) Wellesley/Lincoln-Sudbury Raiders | Wellesley Sports Center |
| February 02, 2021 | (5) Natick Red Hawks at (3) Walpole Timberwolves | Rodman Arena |
| February 06, 2021 | (4) Natick Red Hawks at (2) Walpole Timberwolves | Rodman Arena |
| February 08, 2021 | (0) Braintree Wamps at (1) Walpole Timberwolves | Rodman Arena |
| February 10, 2021 | (2) Walpole Timberwolves at (4) Braintree Wamps | Zapustas Arena |
| February 10, 2021 | (4) Braintree Wamps at (2) Walpole Timberwolves | Rodman Arena |
