| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (1) Winchester Red & Black at (0) Milton Wildcats | Ulin Memorial Rink |
| December 11, 2018 | (0) Milton Wildcats at (3) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| December 15, 2018 | (3) Framingham Flyers at (7) Milton Wildcats | Ulin Memorial Rink |
| December 19, 2018 | (0) Milton Wildcats at (8) Braintree Wamps | Zapustas Arena |
| December 21, 2018 | (0) Milton Wildcats at (8) Walpole Timberwolves | Rodman Arena |
| December 27, 2018 | (1) Milton Wildcats at (4) Westwood Wolverines | Canton Ice House |
| December 29, 2018 | (3) Milton Wildcats at (1) Medfield Warriors
Canton Ice House Tournament |
Canton Ice House |
| January 02, 2019 | (6) Needham Rockets at (3) Milton Wildcats | Ulin Memorial Rink |
| January 05, 2019 | (2) Milton Wildcats at (10) Natick Red Hawks | Chase Arena |
| January 12, 2019 | (3) Weymouth Wildcats at (3) Milton Wildcats | Ulin Memorial Rink |
| January 16, 2019 | (2) Newton North/South Tigers at (2) Milton Wildcats | Ulin Memorial Rink |
| January 21, 2019 | (2) Milton Wildcats at (4) Acton-Boxboro Revolution | Nashoba Valley Olympia |
| January 23, 2019 | (6) Braintree Wamps at (0) Milton Wildcats | Ulin Memorial Rink |
| January 26, 2019 | (4) Wellesley / Lincoln Sudbury Raiders at (1) Milton Wildcats | Ulin Memorial Rink |
| January 30, 2019 | (0) Milton Wildcats at (7) Needham Rockets | Babson Skating Center |
| February 02, 2019 | (5) Notre Dame Academy (Hingham) Cougars at (0) Milton Wildcats | Ulin Memorial Rink |
| February 06, 2019 | (7) Milton Wildcats at (3) Brookline Warriors | Walter Brown Arena |
| February 09, 2019 | (3) Milton Wildcats at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 13, 2019 | (7) Walpole Timberwolves at (0) Milton Wildcats | Ulin Memorial Rink |
| February 16, 2019 | (4) MOA Warriors at (1) Milton Wildcats | Ulin Memorial Rink |
| February 18, 2019 | (2) Milton Wildcats at (3) Winchester Red & Black | O'Brien Arena |
| February 20, 2019 | (1) Woburn Tanners at (0) Milton Wildcats | Ulin Memorial Rink |
