| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 5:30 PM | (1) Milton Wildcats at (1) Wellesley Raiders | Boston Sports Institute |
| Dec. 21, 5:30 PM | (1) Brookline Warriors at (1) Wellesley Raiders | Wellesley Sports Center |
| Dec. 23, 6:00 PM | (3) Wellesley Raiders at (4) Needham Rockets | Babson Skating Center |
| Dec. 27, 5:00 PM | (5) Essex Tech Hawks at (3) Wellesley Raiders
Ryan Kenney Christmas Classic |
Falmouth Ice Arena |
| Dec. 28, 11:59 PM | TBD - Ryan Kenney Classic - Falmouth or Plymouth South at Wellesley Raiders
Ryan Kenney Classic |
Falmouth Ice Arena |
| Jan. 4, 5:00 PM | Wellesley Raiders at Framingham Flyers | Loring Arena |
| Jan. 8, 7:40 PM | Wellesley Raiders at Natick Red Hawks | Chase Arena |
| Jan. 11, 12:00 PM | Wellesley Raiders at Walpole Timberwolves | Cadillac Ice Arena |
| Jan. 15, 6:15 PM | Needham Rockets at Wellesley Raiders | Boston Sports Institute |
| Jan. 25, 5:30 PM | Weymouth Wildcats at Wellesley Raiders | Boston Sports Institute |
| Jan. 29, 6:00 PM | Wellesley Raiders at Braintree Wamps | Zapustas Arena |
| Feb. 1, 5:30 PM | Newton North Tigers at Wellesley Raiders | Boston Sports Institute |
| Feb. 5, 7:45 PM | Wellesley Raiders at Brookline Warriors | John A. Ryan Arena |
| Feb. 8, 5:30 PM | Framingham Flyers at Wellesley Raiders | Boston Sports Institute |
| Feb. 12, 6:15 PM | Natick Red Hawks at Wellesley Raiders | Boston Sports Institute |
| Feb. 17, 3:20 PM | Wellesley Raiders at Marshfield Rams | The Bog |
