| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (1) Walpole Timberwolves at (4) Mansfield Hornets | Foxboro Sports Center |
| December 15, 2018 | (2) Newton North Tigers at (4) Walpole Timberwolves | Rodman Arena |
| December 19, 2018 | (3) Needham Rockets at (1) Walpole Timberwolves | Rodman Arena |
| December 22, 2018 | (2) Walpole Timberwolves at (2) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| December 26, 2018 | (2) Lowell Catholic Crusaders at (2) Walpole Timberwolves
SONGIN CUP |
Rodman Arena |
| December 28, 2018 | (0) Shrewsbury Colonials at (3) Walpole Timberwolves
Songin Winter Classic |
Rodman Arena |
| December 31, 2018 | (3) Walpole Timberwolves at (1) Norwood Mustangs | Bajko Memorial Rink |
| January 02, 2019 | (3) Walpole Timberwolves at (2) Weymouth Wildcats | Connell Memorial Rink |
| January 09, 2019 | (1) Braintree Wamps at (3) Walpole Timberwolves | Rodman Arena |
| January 16, 2019 | (2) Brookline Warriors at (5) Walpole Timberwolves | Rodman Arena |
| January 19, 2019 | (4) Walpole Timberwolves at (1) Milton Wildcats | Ulin Memorial Rink |
| January 23, 2019 | (2) Walpole Timberwolves at (5) Needham Rockets | Babson Skating Center |
| January 26, 2019 | (0) Walpole Timberwolves at (3) Framingham Flyers | Loring Arena |
| January 30, 2019 | (1) Weymouth Wildcats at (4) Walpole Timberwolves | Rodman Arena |
| February 02, 2019 | (3) Walpole Timberwolves at (3) Braintree Wamps | Zapustas Arena |
| February 06, 2019 | (4) Walpole Timberwolves at (0) Natick Red Hawks | Chase Arena |
| February 09, 2019 | (4) Mansfield Hornets at (3) Walpole Timberwolves | Rodman Arena |
| February 11, 2019 | (2) Walpole Timberwolves at (4) Burlington Red Devils | Burlington Ice Palace |
| February 13, 2019 | (2) Milton Wildcats at (3) Walpole Timberwolves | Rodman Arena |
| February 16, 2019 | (3) King Philip Warriors at (4) Walpole Timberwolves | Rodman Arena |
| February 19, 2019 | (1) Wellesley Raiders at (0) Walpole Timberwolves | Rodman Arena |
| February 21, 2019 | (7) Walpole Timberwolves at (1) Brockton Boxers | Asiaf Skating Arena |
| February 27, 2019 | (3) Wellesley Raiders at (0) Walpole Timberwolves | Canton Ice House |
