| Date & Time | Game | Venue |
|---|---|---|
| December 10, 2018 | (1) Wellesley Raiders at (4) Arlington Spy Ponders | Ed Burns Arena |
| December 15, 2018 | (3) Wellesley Raiders at (0) Weymouth Wildcats | Connery Memorial Arena |
| December 19, 2018 | (3) Wellesley Raiders at (1) Shrewsbury Colonials | NorthStar Ice Sports |
| December 31, 2018 | (0) Wellesley Raiders at (3) Austin Prep Cougars | Merrimack College |
| January 02, 2019 | (0) Framingham Flyers at (5) Wellesley Raiders | Babson Skating Center |
| January 09, 2019 | (2) Wellesley Raiders at (0) Brookline Warriors | Walter Brown Arena |
| January 12, 2019 | (9) Wellesley Raiders at (0) Newton North/South Tigers | John A. Ryan Arena |
| January 16, 2019 | (3) Needham Rockets at (3) Wellesley Raiders | Babson Skating Center |
| January 19, 2019 | (1) Natick Red Hawks at (3) Wellesley Raiders | Babson Skating Center |
| January 21, 2019 | (1) Walpole Timberwolves at (1) Wellesley Raiders
postponed from 1/5/19 |
Babson Skating Center |
| January 26, 2019 | (4) Wellesley Raiders at (1) Milton Wildcats | Ulin Memorial Rink |
| January 28, 2019 | (1) Notre Dame Academy (Hingham) Cougars at (1) Wellesley Raiders | Babson Skating Center |
| January 30, 2019 | (7) Wellesley Raiders at (1) Framingham Flyers | Loring Arena |
| February 01, 2019 | (2) Wellesley Raiders at (3) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| February 02, 2019 | (0) Brookline Warriors at (4) Wellesley Raiders | Babson Skating Center |
| February 06, 2019 | (1) Braintree Wamps at (3) Wellesley Raiders | Babson Skating Center |
| February 09, 2019 | (0) Newton North/South Tigers at (4) Wellesley Raiders | Babson Skating Center |
| February 13, 2019 | (4) Wellesley Raiders at (0) Natick Red Hawks | Chase Arena |
| February 17, 2019 | (8) Wellesley Raiders at (0) Needham Rockets | Daly Memorial Rink |
| February 20, 2019 | (6) Austin Prep Cougars at (2) Wellesley Raiders | Babson Skating Center |
| March 04, 2019 | (0) Canton Bulldogs at (5) Wellesley Raiders | John A. Ryan Arena |
| March 07, 2019 | (6) Wellesley Raiders at (1) Norwell | Warrior Ice Arena |
| March 12, 2019 | (4) Wellesley Raiders at (1) Walpole Timberwolves | Warrior Ice Arena |
| March 17, 2019 | (2) Notre Dame Academy (Hingham) Cougars at (3) Wellesley Raiders | TD Garden |
