| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (2) Natick Red Hawks at (6) Wellesley Raiders | Boston Sports Institute |
| December 16, 2023 | (4) Wellesley Raiders at (5) Milton Wildcats | Ulin Memorial Rink |
| December 20, 2023 | (1) Newton North Tigers at (8) Wellesley Raiders | Boston Sports Institute |
| December 23, 2023 | (6) Wellesley Raiders at (5) Needham Rockets | Babson Skating Center |
| December 27, 2023 | (3) Plymouth South Panthers at (5) Wellesley Raiders
Ray Kenney Classic |
Falmouth Ice Arena |
| December 28, 2023 | (5) Wellesley Raiders at (4) Falmouth Clippers
Ray Kenney Christmas Classic Finals |
Falmouth Ice Arena |
| January 03, 2024 | (2) Lincoln-Sudbury Warriors at (0) Wellesley Raiders | Boston Sports Institute |
| January 06, 2024 | (1) Wellesley Raiders at (1) Brookline Warriors
OT game ends in a tie |
Walter Brown Arena |
| January 10, 2024 | (3) Framingham Flyers at (5) Wellesley Raiders | Boston Sports Institute |
| January 13, 2024 | (1) Wellesley Raiders at (1) Framingham Flyers
OT game ends in a tie |
Loring Arena |
| January 15, 2024 | (5) Wellesley Raiders at (3) Weymouth Wildcats | Connell Memorial Rink |
| January 24, 2024 | (1) Walpole Timberwolves at (4) Wellesley Raiders | Boston Sports Institute |
| January 26, 2024 | (0) Needham Rockets at (2) Wellesley Raiders | Boston Sports Institute |
| January 28, 2024 | (4) Walpole Timberwolves at (3) Wellesley Raiders
Ed Burns Coffee Pot |
Canton Ice House |
| January 31, 2024 | (2) Braintree Wamps at (3) Wellesley Raiders | Boston Sports Institute |
| February 04, 2024 | (1) Chelmsford Lions at (6) Wellesley Raiders
Ed Burns Coffe Pot Classic - Consolation Semi Finals |
Chelmsford Forum |
| February 07, 2024 | (0) Brookline Warriors at (7) Wellesley Raiders | Boston Sports Institute |
| February 11, 2024 | (1) Wellesley Raiders at (4) Reading Rockets
Ed Burns Coffee Pot |
John A. Ryan Arena |
| February 14, 2024 | (4) Wellesley Raiders at (0) Natick Red Hawks | Chase Arena |
| February 20, 2024 | (1) Marshfield Rams at (3) Wellesley Raiders | Boston Sports Institute |
| February 28, 2024 | (2) Belmont Marauders at (3) Wellesley Raiders
MIAA D1 BOYS STATE TOURNAMENT - Round 32 |
Boston Sports Institute |
| March 02, 2024 | (1) Wellesley Raiders at (7) St. John's Prep Eagles
MIAA D1 BOYS STATE TOURNAMENT - SWEET 16 |
Essex Sports Center |
