| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) Milton Wildcats at (3) Ursuline Academy Bears | Jim Roche Community Arena |
| December 14, 2019 | (2) Milton Wildcats at (1) Framingham Flyers | Loring Arena |
| December 18, 2019 | (5) Braintree Wamps at (0) Milton Wildcats | Ulin Memorial Rink |
| December 21, 2019 | (0) Milton Wildcats at (6) Needham Rockets | Babson Skating Center |
| December 23, 2019 | (5) Norwood Mustangs at (1) Milton Wildcats | Ulin Memorial Rink |
| December 27, 2019 | (0) Milton Wildcats at (4) Westwood Wolverines
CANTON ICE HOUSE TOURNAMENT |
Canton Ice House |
| December 29, 2019 | (1) Medfield Warriors at (2) Milton Wildcats
Canton Ice House Tournament |
Canton Ice House |
| December 31, 2019 | (4) Notre Dame Academy (Hingham) Cougars at (1) Milton Wildcats | Ulin Memorial Rink |
| January 04, 2020 | (2) Natick Red Hawks at (1) Milton Wildcats | Ulin Memorial Rink |
| January 08, 2020 | (1) Plymouth Blue Eagles at (1) Milton Wildcats | Ulin Memorial Rink |
| January 11, 2020 | (5) Milton Wildcats at (3) Weymouth Wildcats | Connell Memorial Rink |
| January 15, 2020 | (4) Milton Wildcats at (1) Newton North/South Tigers | John A. Ryan Arena |
| January 18, 2020 | (3) Walpole Timberwolves at (2) Milton Wildcats | Ulin Memorial Rink |
| January 22, 2020 | (1) Milton Wildcats at (10) Braintree Wamps | Zapustas Arena |
| January 25, 2020 | (0) Milton Wildcats at (3) Wellesley Raiders | Wellesley Sports Center |
| January 29, 2020 | (4) Needham Rockets at (1) Milton Wildcats | Ulin Memorial Rink |
| February 05, 2020 | (1) Brookline Warriors at (1) Milton Wildcats | Ulin Memorial Rink |
| February 08, 2020 | (0) Weymouth Wildcats at (3) Milton Wildcats | Ulin Memorial Rink |
| February 12, 2020 | (1) Milton Wildcats at (2) Walpole Timberwolves | Rodman Arena |
| February 15, 2020 | (0) Milton Wildcats at (3) Notre Dame Academy (Hingham) Cougars | Rockland Arena |
| February 17, 2020 | (2) Quincy/North Quincy Red Raiders at (7) Milton Wildcats | Ulin Memorial Rink |
