| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (5) Framingham Flyers at (4) Milton Wildcats | Ulin Memorial Rink |
| December 18, 2019 | (3) Milton Wildcats at (3) Braintree Wamps | Zapustas Arena |
| December 21, 2019 | (5) Needham Rockets at (1) Milton Wildcats | Ulin Memorial Rink |
| December 26, 2019 | (2) Milton Wildcats at (4) King Philip Warriors
Qunicy Holiday Tournament |
Quincy Youth Arena |
| December 28, 2019 | (0) Quincy Presidents at (4) Milton Wildcats
Quincy Tournament |
Quincy Youth Arena |
| December 31, 2019 | (2) Milton Wildcats at (5) Waltham Hawks | Veterans Memorial Rink |
| January 04, 2020 | (2) Milton Wildcats at (2) Natick Red Hawks | Chase Arena |
| January 11, 2020 | (4) Weymouth Wildcats at (1) Milton Wildcats | Ulin Memorial Rink |
| January 15, 2020 | (1) Newton North Tigers at (3) Milton Wildcats | Ulin Memorial Rink |
| January 18, 2020 | (4) Walpole Timberwolves at (1) Milton Wildcats | Ulin Memorial Rink |
| January 20, 2020 | (2) Milton Wildcats at (2) Norwood Mustangs | Bajko Memorial Rink |
| January 22, 2020 | (9) Braintree Wamps at (0) Milton Wildcats | Ulin Memorial Rink |
| January 25, 2020 | (0) Wellesley Raiders at (4) Milton Wildcats | Ulin Memorial Rink |
| January 29, 2020 | (2) Milton Wildcats at (1) Needham Rockets | Babson Skating Center |
| February 01, 2020 | (5) Archbishop Williams Bishops at (3) Milton Wildcats | Ulin Memorial Rink |
| February 05, 2020 | (5) Milton Wildcats at (4) Brookline Warriors | Walter Brown Arena |
| February 08, 2020 | (3) Milton Wildcats at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 12, 2020 | (3) Milton Wildcats at (1) Walpole Timberwolves | Rodman Arena |
| February 15, 2020 | (3) Bridgewater-Raynham Trojans at (2) Milton Wildcats | Ulin Memorial Rink |
| February 18, 2020 | (2) Milton Wildcats at (5) Westford Academy Ghosts
Irish American Shootout |
O'Brien Arena |
| February 20, 2020 | (1) Milton Wildcats at (1) Billerica Indians
Irish American Shootout consolation |
O'Brien Arena |
| February 26, 2020 | (2) Milton Wildcats at (4) Natick Red Hawks
Boys D1 S Playoff |
John A. Ryan Arena |
