| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (4) Walpole Timberwolves at (1) King Philip Warriors | Foxboro Sports Center |
| December 15, 2018 | (6) Walpole Timberwolves at (1) Newton North/South Tigers | John A. Ryan Arena |
| December 19, 2018 | (1) Walpole Timberwolves at (2) Needham Rockets | Babson Skating Center |
| December 21, 2018 | (0) Milton Wildcats at (8) Walpole Timberwolves | Rodman Arena |
| December 27, 2018 | (5) Walpole Timberwolves at (0) MOA Warriors | Foxboro Sports Center |
| December 31, 2018 | (3) Walpole Timberwolves at (1) Norwood Mustangs | Bajko Memorial Rink |
| January 02, 2019 | (1) Weymouth Wildcats at (5) Walpole Timberwolves | Rodman Arena |
| January 09, 2019 | (1) Walpole Timberwolves at (4) Braintree Wamps | Zapustas Arena |
| January 14, 2019 | (3) Walpole Timberwolves at (1) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| January 16, 2019 | (4) Walpole Timberwolves at (2) Brookline Warriors | Walter Brown Arena |
| January 21, 2019 | (1) Walpole Timberwolves at (1) Wellesley Raiders
postponed from 1/5/19 |
Babson Skating Center |
| January 23, 2019 | (1) Needham Rockets at (4) Walpole Timberwolves | Rodman Arena |
| January 26, 2019 | (2) Framingham Flyers at (8) Walpole Timberwolves | Rodman Arena |
| January 28, 2019 | (1) Franklin Panthers at (3) Walpole Timberwolves | Rodman Arena |
| January 30, 2019 | (5) Walpole Timberwolves at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 02, 2019 | (3) Braintree Wamps at (1) Walpole Timberwolves | Rodman Arena |
| February 06, 2019 | (1) Natick Red Hawks at (2) Walpole Timberwolves | Rodman Arena |
| February 13, 2019 | (7) Walpole Timberwolves at (0) Milton Wildcats | Ulin Memorial Rink |
| February 18, 2019 | (0) King Philip Warriors at (3) Walpole Timberwolves | Rodman Arena |
| February 21, 2019 | (2) Walpole Timberwolves at (1) Canton Bulldogs | Canton Ice House |
| March 03, 2019 | (1) Winchester Red & Black at (2) Walpole Timberwolves
Overtime |
Canton Ice House |
| March 07, 2019 | (1) Matignon Warriors at (4) Walpole Timberwolves | O'Brien Arena |
| March 12, 2019 | (4) Wellesley Raiders at (1) Walpole Timberwolves | Warrior Ice Arena |
