| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (2) Walpole Timberwolves at (3) Weymouth Wildcats | Connell Memorial Rink |
| December 16, 2023 | (3) Walpole Timberwolves at (2) Braintree Wamps | Zapustas Arena |
| December 20, 2023 | (3) Milton Wildcats at (0) Walpole Timberwolves | Rodman Arena |
| December 27, 2023 | (3) Walpole Timberwolves at (5) Norwood Mustangs | The Skating Club of Boston |
| January 03, 2024 | (2) Walpole Timberwolves at (2) Waltham Hawks | Veterans Memorial Rink |
| January 06, 2024 | (3) Framingham Flyers at (2) Walpole Timberwolves | Rodman Arena |
| January 10, 2024 | (3) Needham Rockets at (0) Walpole Timberwolves | Rodman Arena |
| January 18, 2024 | (0) Walpole Timberwolves at (1) Newton North Tigers | John A. Ryan Arena |
| January 24, 2024 | (1) Walpole Timberwolves at (4) Wellesley Raiders | Boston Sports Institute |
| January 27, 2024 | (6) Walpole Timberwolves at (1) Brookline Warriors | Walter Brown Arena |
| January 28, 2024 | (4) Walpole Timberwolves at (3) Wellesley Raiders
Ed Burns Coffee Pot |
Canton Ice House |
| January 31, 2024 | (1) Weymouth Wildcats at (4) Walpole Timberwolves | Rodman Arena |
| February 03, 2024 | (2) Braintree Wamps at (0) Walpole Timberwolves | Rodman Arena |
| February 04, 2024 | (4) Belmont Marauders at (0) Walpole Timberwolves
Ed Burns Coffee Pot Classic - Brinn Division Semifinals |
Rodman Arena |
| February 07, 2024 | (1) Walpole Timberwolves at (4) Milton Wildcats | Ulin Memorial Rink |
| February 10, 2024 | (0) Natick Red Hawks at (4) Walpole Timberwolves | Rodman Arena |
| February 11, 2024 | (4) Walpole Timberwolves at (0) Chelmsford Lions
Ed Burns Coffee Pot |
Canton Ice House |
| February 14, 2024 | (4) Walpole Timberwolves at (2) Needham Rockets | Babson Skating Center |
| February 17, 2024 | (3) Mansfield Hornets at (6) Walpole Timberwolves
Songin Cup |
Rodman Arena |
| February 19, 2024 | (4) King Philip Warriors at (1) Walpole Timberwolves
Songin Cup |
Rodman Arena |
| February 28, 2024 | (2) Walpole Timberwolves at (6) Gloucester Fishermen
Miaa D2 BOYS STATE TOURNAMENT - Round 32 |
Dorothy Talbot Rink |
