| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2018 | (1) Weymouth Wildcats at (2) Wellesley Raiders | Babson Skating Center |
| December 19, 2018 | (0) Wellesley Raiders at (3) Falmouth Clippers | Falmouth Ice Arena |
| December 22, 2018 | (1) Wellesley Raiders at (2) Needham Rockets | Babson Skating Center |
| December 27, 2018 | (1) Wellesley Raiders at (1) Hanover Hawks
Unkie Christmas Tournament |
Stoneham Arena |
| December 28, 2018 | (6) Wellesley Raiders at (0) Matignon Warriors
Unkie Fitzgerald Christmas Tournament |
Stoneham Arena |
| January 02, 2019 | (0) Wellesley Raiders at (2) Framingham Flyers | Loring Arena |
| January 07, 2019 | (1) North Attleboro Red Rocketeers at (3) Wellesley Raiders | Babson Skating Center |
| January 09, 2019 | (3) Wellesley Raiders at (1) Brookline Warriors | Walter Brown Arena |
| January 12, 2019 | (1) Newton North Tigers at (2) Wellesley Raiders | Babson Skating Center |
| January 16, 2019 | (1) Needham Rockets at (2) Wellesley Raiders | Babson Skating Center |
| January 19, 2019 | (1) Wellesley Raiders at (3) Natick Red Hawks | Chase Arena |
| January 21, 2019 | (3) Wellesley Raiders at (1) Triton Vikings | Graf Rink |
| January 23, 2019 | (1) Concord-Carlisle Patriots at (0) Wellesley Raiders | Babson Skating Center |
| January 26, 2019 | (1) Milton Wildcats at (1) Wellesley Raiders | Babson Skating Center |
| January 30, 2019 | (2) Framingham Flyers at (1) Wellesley Raiders | Babson Skating Center |
| February 06, 2019 | (1) Wellesley Raiders at (2) Braintree Wamps | Zapustas Arena |
| February 09, 2019 | (2) Wellesley Raiders at (0) Newton North Tigers | John A. Ryan Arena |
| February 13, 2019 | (1) Natick Red Hawks at (6) Wellesley Raiders | Babson Skating Center |
| February 19, 2019 | (1) Wellesley Raiders at (0) Walpole Timberwolves | Rodman Arena |
| February 21, 2019 | (4) Wellesley Raiders at (1) Waltham Hawks | Veterans Memorial Rink |
| February 27, 2019 | (3) Wellesley Raiders at (0) Walpole Timberwolves | Canton Ice House |
| March 02, 2019 | (0) Wellesley Raiders at (2) Duxbury Dragons | Canton Ice House |
