| Date & Time | Game | Venue |
|---|---|---|
| Dec. 11, 6:10 PM | (2) North Attleboro Red Rocketeers at (5) Wellesley Raiders | Boston Sports Institute |
| Dec. 13, 6:00 PM | (0) Wellesley Raiders at (4) Milton Wildcats | Ulin Memorial Rink |
| Dec. 17, 6:00 PM | Newton North Tigers at Wellesley Raiders | Wellesley Sports Center |
| Dec. 20, 3:00 PM | Wellesley Raiders at Brookline Warriors | Walter Brown Arena |
| Dec. 23, 4:00 PM | Needham Rockets at Wellesley Raiders | Wellesley Sports Center |
| Dec. 27, 7:00 PM | Wellesley Raiders at Falmouth Clippers
Ray Kenney Classic |
Falmouth Ice Arena |
| Dec. 28 (Time TBA) | Wellesley Raiders at TBD
Ray Kenny Christmas Classic |
Falmouth Ice Arena |
| Jan. 3, 5:30 PM | Framingham Flyers at Wellesley Raiders | Wellesley Sports Center |
| Jan. 7, 8:00 PM | Walpole Timberwolves at Wellesley Raiders | Wellesley Sports Center |
| Jan. 10, 11:30 AM | Wellesley Raiders at Needham Rockets | Babson Skating Center |
| Jan. 14, 6:15 PM | Natick Red Hawks at Wellesley Raiders | Wellesley Sports Center |
| Jan. 19, 4:00 PM | North Middlesex Patriots at Wellesley Raiders | Wellesley Sports Center |
| Jan. 24, 7:20 PM | Wellesley Raiders at Weymouth Wildcats | Connell Memorial Rink |
| Jan. 28, 6:15 PM | Braintree Wamps at Wellesley Raiders | Wellesley Sports Center |
| Jan. 31, 12:20 PM | Wellesley Raiders at Newton North Tigers | John A. Ryan Arena |
| Feb. 4, 6:15 PM | Brookline Warriors at Wellesley Raiders | Wellesley Sports Center |
| Feb. 7, 6:00 PM | Wellesley Raiders at Framingham Flyers | Loring Arena |
| Feb. 8, 6:00 PM | Wellesley Raiders at North Attleboro Red Rocketeers | New England Sports Village |
| Feb. 11, 7:40 PM | Wellesley Raiders at Natick Red Hawks | Chase Arena |
| Feb. 16, 4:00 PM | Plymouth North Eagles at Wellesley Raiders | Wellesley Sports Center |
