| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (0) Milton Wildcats at (2) Needham Rockets | Babson Skating Center |
| December 16, 2023 | (4) Wellesley Raiders at (5) Milton Wildcats | Ulin Memorial Rink |
| December 20, 2023 | (3) Milton Wildcats at (0) Walpole Timberwolves | Rodman Arena |
| December 23, 2023 | (4) Canton Bulldogs at (4) Milton Wildcats | Ulin Memorial Rink |
| December 26, 2023 | (2) King Philip Warriors at (2) Milton Wildcats
Quincy Youth Holiday Tournament |
Quincy Youth Arena |
| December 28, 2023 | (5) Milton Wildcats at (2) North Quincy Red Raiders
Quincy Youth Holiday Tournament |
Quincy Youth Arena |
| January 06, 2024 | (4) Weymouth Wildcats at (2) Milton Wildcats | Ulin Memorial Rink |
| January 10, 2024 | (0) Milton Wildcats at (3) Braintree Wamps | Zapustas Arena |
| January 13, 2024 | (3) Natick Red Hawks at (2) Milton Wildcats | Ulin Memorial Rink |
| January 15, 2024 | (5) Archbishop Williams Bishops at (4) Milton Wildcats | Ulin Memorial Rink |
| January 20, 2024 | (1) Framingham Flyers at (2) Milton Wildcats | Ulin Memorial Rink |
| January 24, 2024 | (1) Milton Wildcats at (3) Natick Red Hawks | Chase Arena |
| January 31, 2024 | (1) Needham Rockets at (1) Milton Wildcats | Ulin Memorial Rink |
| February 03, 2024 | (2) Milton Wildcats at (2) Brookline Warriors | Walter Brown Arena |
| February 07, 2024 | (1) Walpole Timberwolves at (4) Milton Wildcats | Ulin Memorial Rink |
| February 10, 2024 | (4) Weymouth Wildcats at (3) Milton Wildcats | Connell Memorial Rink |
| February 14, 2024 | (3) Braintree Wamps at (2) Milton Wildcats
Braintree wins in OT |
Ulin Memorial Rink |
| February 19, 2024 | (0) Newton North Tigers at (0) Milton Wildcats
Postponed from 1/27/24 |
Ulin Memorial Rink |
| February 20, 2024 | (0) Milton Wildcats at (0) Westford Academy Ghosts
Irish American Shootout |
Hobomock Arena |
| February 29, 2024 | (2) Milton Wildcats at (3) North Andover Scarlet Knights
MIAA D2 BOYS STATE TOURNAMENT - Round 32 |
Brooks School Rink |
