| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 6:15 PM | (2) Natick Red Hawks at (6) Wellesley Raiders | Boston Sports Institute |
| Dec. 16, 6:00 PM | (4) Wellesley Raiders at (5) Milton Wildcats | Ulin Memorial Rink |
| Dec. 20, 6:15 PM | (1) Newton North Tigers at (8) Wellesley Raiders | Boston Sports Institute |
| Dec. 23, 3:00 PM | (6) Wellesley Raiders at (5) Needham Rockets | Babson Skating Center |
| Dec. 27, 5:00 PM | (3) Plymouth South Panthers at (5) Wellesley Raiders
Ray Kenney Classic |
Falmouth Ice Arena |
| Dec. 28, 7:00 PM | (5) Wellesley Raiders at (4) Falmouth Clippers
Ray Kenney Christmas Classic Finals |
Falmouth Ice Arena |
| Jan. 3, 6:15 PM | (2) Lincoln-Sudbury Warriors at (0) Wellesley Raiders | Boston Sports Institute |
| Jan. 6, 12:00 PM | (1) Wellesley Raiders at (1) Brookline Warriors
OT game ends in a tie |
Walter Brown Arena |
| Jan. 10, 6:15 PM | (3) Framingham Flyers at (5) Wellesley Raiders | Boston Sports Institute |
| Jan. 13, 5:00 PM | (1) Wellesley Raiders at (1) Framingham Flyers
OT game ends in a tie |
Loring Arena |
| Jan. 15, 3:00 PM | (5) Wellesley Raiders at (3) Weymouth Wildcats | Connell Memorial Rink |
| Jan. 24, 6:15 PM | (1) Walpole Timberwolves at (4) Wellesley Raiders | Boston Sports Institute |
| Jan. 26, 4:00 PM | (0) Needham Rockets at (2) Wellesley Raiders | Boston Sports Institute |
| Jan. 28, 12:00 PM | (4) Walpole Timberwolves at (3) Wellesley Raiders
Ed Burns Coffee Pot |
Canton Ice House |
| Jan. 31, 6:15 PM | (2) Braintree Wamps at (3) Wellesley Raiders | Boston Sports Institute |
| Feb. 4, 5:20 PM | (1) Chelmsford Lions at (6) Wellesley Raiders
Ed Burns Coffe Pot Classic - Consolation Semi Finals |
Chelmsford Forum |
| Feb. 7, 6:15 PM | (0) Brookline Warriors at (7) Wellesley Raiders | Boston Sports Institute |
| Feb. 11, 4:00 PM | (1) Wellesley Raiders at (4) Reading Rockets
Ed Burns Coffee Pot |
John A. Ryan Arena |
| Feb. 14, 7:40 PM | (4) Wellesley Raiders at (0) Natick Red Hawks | Chase Arena |
| Feb. 20, 4:00 PM | (1) Marshfield Rams at (3) Wellesley Raiders | Boston Sports Institute |
| Feb. 28, 7:15 PM | (2) Belmont Marauders at (3) Wellesley Raiders
MIAA D1 BOYS STATE TOURNAMENT - Round 32 |
Boston Sports Institute |
| Mar. 2, 2:30 PM | (1) Wellesley Raiders at (7) St. John's Prep Eagles
MIAA D1 BOYS STATE TOURNAMENT - SWEET 16 |
Essex Sports Center |
