| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Wellesley Raiders at (1) Weymouth Wildcats | Connell Memorial Rink |
| December 16, 2019 | (4) Cambridge Rindge & Latin Falcons at (0) Wellesley Raiders | Wellesley Sports Center |
| December 21, 2019 | (2) Framingham Flyers at (0) Wellesley Raiders | Wellesley Sports Center |
| December 23, 2019 | (0) Needham Rockets at (1) Wellesley Raiders | Babson Skating Center |
| December 27, 2019 | (3) Wellesley Raiders at (0) Westford Academy Ghosts
Cape Cod Cup |
Falmouth Ice Arena |
| December 28, 2019 | (0) Newton South Lions at (2) Wellesley Raiders
Ray Kenney - Cape Cod Cup |
Falmouth Ice Arena |
| January 02, 2020 | (3) Walpole Timberwolves at (3) Wellesley Raiders | Babson Skating Center |
| January 11, 2020 | (2) Wellesley Raiders at (0) Newton North Tigers | John A. Ryan Arena |
| January 15, 2020 | (3) Wellesley Raiders at (2) Needham Rockets | Babson Skating Center |
| January 18, 2020 | (1) Natick Red Hawks at (0) Wellesley Raiders | Wellesley Sports Center |
| January 20, 2020 | (1) North Attleboro Red Rocketeers at (4) Wellesley Raiders | Wellesley Sports Center |
| January 25, 2020 | (0) Wellesley Raiders at (4) Milton Wildcats | Ulin Memorial Rink |
| January 27, 2020 | (2) Triton Vikings at (1) Wellesley Raiders | Wellesley Sports Center |
| January 29, 2020 | (0) Wellesley Raiders at (1) Framingham Flyers | Loring Arena |
| February 01, 2020 | (1) Wellesley Raiders at (2) Brookline Warriors | Walter Brown Arena |
| February 05, 2020 | (2) Braintree Wamps at (5) Wellesley Raiders | Wellesley Sports Center |
| February 08, 2020 | (0) Newton North Tigers at (3) Wellesley Raiders | Wellesley Sports Center |
| February 12, 2020 | (2) Wellesley Raiders at (2) Natick Red Hawks | Chase Arena |
| February 15, 2020 | (2) Concord-Carlisle Patriots at (5) Wellesley Raiders | Wellesley Sports Center |
| February 19, 2020 | (5) Waltham Hawks at (1) Wellesley Raiders | Babson Skating Center |
| February 27, 2020 | (2) Wellesley Raiders at (0) Marshfield Rams
Boys D1 S Playoff |
Gallo Arena |
| February 29, 2020 | (1) Wellesley Raiders at (2) Archbishop Williams Bishops
Boys D1 S Playoff |
Canton Ice House |
