| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (0) Newton North/South Tigers at (1) Walpole Timberwolves | Rodman Arena |
| December 18, 2019 | (6) Needham Rockets at (1) Walpole Timberwolves | Rodman Arena |
| December 21, 2019 | (7) Walpole Timberwolves at (3) Weymouth Wildcats | Connell Memorial Rink |
| December 26, 2019 | (7) MOA Warriors at (5) Walpole Timberwolves | Rodman Arena |
| December 31, 2019 | (3) Norwood Mustangs at (6) Walpole Timberwolves | Rodman Arena |
| January 02, 2020 | (7) Wellesley Raiders at (1) Walpole Timberwolves | Rodman Arena |
| January 08, 2020 | (1) Walpole Timberwolves at (5) Braintree Wamps | Zapustas Arena |
| January 13, 2020 | (6) King Philip Warriors at (2) Walpole Timberwolves | Rodman Arena |
| January 15, 2020 | (2) Brookline Warriors at (4) Walpole Timberwolves | Rodman Arena |
| January 18, 2020 | (3) Walpole Timberwolves at (2) Milton Wildcats | Ulin Memorial Rink |
| January 22, 2020 | (1) Walpole Timberwolves at (3) Needham Rockets | Babson Skating Center |
| January 25, 2020 | (2) Walpole Timberwolves at (1) Framingham Flyers | Loring Arena |
| January 29, 2020 | (1) Weymouth Wildcats at (4) Walpole Timberwolves | Rodman Arena |
| February 01, 2020 | (6) Braintree Wamps at (1) Walpole Timberwolves | Rodman Arena |
| February 05, 2020 | (0) Walpole Timberwolves at (5) Natick Red Hawks | Chase Arena |
| February 12, 2020 | (1) Milton Wildcats at (2) Walpole Timberwolves | Rodman Arena |
| February 15, 2020 | (3) Walpole Timberwolves at (4) MOA Warriors | Rodman Arena |
| February 17, 2020 | (0) Walpole Timberwolves at (3) King Philip Warriors | Foxboro Sports Center |
| February 19, 2020 | (4) Canton Bulldogs at (0) Walpole Timberwolves | Rodman Arena |
