| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (5) Norwell at (1) Weymouth Wildcats | Connell Memorial Rink |
| December 14, 2019 | (0) Weymouth Wildcats at (7) Wellesley Raiders | Wellesley Sports Center |
| December 18, 2019 | (1) Bishop Feehan Shamrocks at (9) Weymouth Wildcats | Connell Memorial Rink |
| December 21, 2019 | (7) Walpole Timberwolves at (3) Weymouth Wildcats | Connell Memorial Rink |
| December 24, 2019 | (0) Weymouth Wildcats at (8) Hingham Harborwomen | Pilgrim Arena |
| December 28, 2019 | (7) Norwood Mustangs at (3) Weymouth Wildcats | Connell Memorial Rink |
| January 01, 2020 | (4) Quincy/North Quincy Red Raiders at (12) Weymouth Wildcats | Connell Memorial Rink |
| January 04, 2020 | (1) Weymouth Wildcats at (3) Brookline Warriors | Walter Brown Arena |
| January 06, 2020 | (0) Weymouth Wildcats at (5) Medway/Ashland Mustangs | Pirelli Veterans Arena |
| January 08, 2020 | (3) Weymouth Wildcats at (10) Needham Rockets | Babson Skating Center |
| January 11, 2020 | (5) Milton Wildcats at (3) Weymouth Wildcats | Connell Memorial Rink |
| January 15, 2020 | (4) Framingham Flyers at (6) Weymouth Wildcats | Connell Memorial Rink |
| January 18, 2020 | (0) Weymouth Wildcats at (8) Braintree Wamps | Zapustas Arena |
| January 22, 2020 | (2) Weymouth Wildcats at (5) Watertown Raiders | John A. Ryan Arena |
| January 25, 2020 | (0) Weymouth Wildcats at (10) Natick Red Hawks | Chase Arena |
| January 29, 2020 | (1) Weymouth Wildcats at (4) Walpole Timberwolves | Rodman Arena |
| February 01, 2020 | (10) Needham Rockets at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 05, 2020 | (2) Newton North/South Tigers at (0) Weymouth Wildcats | Connell Memorial Rink |
| February 08, 2020 | (0) Weymouth Wildcats at (3) Milton Wildcats | Ulin Memorial Rink |
| February 12, 2020 | (7) Braintree Wamps at (0) Weymouth Wildcats | Connell Memorial Rink |
| February 19, 2020 | (1) Marshfield Rams at (2) Weymouth Wildcats | Connell Memorial Rink |
