| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Wellesley Raiders at (1) Weymouth Wildcats | Connell Memorial Rink |
| December 21, 2019 | (2) Weymouth Wildcats at (2) Walpole Timberwolves | Rodman Arena |
| December 22, 2019 | (4) Weymouth Wildcats at (5) Falmouth Clippers | Falmouth Ice Arena |
| December 24, 2019 | (0) Weymouth Wildcats at (3) Hingham Harbormen | Pilgrim Arena |
| December 26, 2019 | (2) Medford Mustangs at (5) Weymouth Wildcats | Connell Memorial Rink |
| January 04, 2020 | (1) Brookline Warriors at (2) Weymouth Wildcats | Connell Memorial Rink |
| January 08, 2020 | (1) Needham Rockets at (3) Weymouth Wildcats | Connell Memorial Rink |
| January 11, 2020 | (4) Weymouth Wildcats at (1) Milton Wildcats | Ulin Memorial Rink |
| January 15, 2020 | (1) Weymouth Wildcats at (5) Framingham Flyers | Loring Arena |
| January 18, 2020 | (3) Braintree Wamps at (1) Weymouth Wildcats | Connell Memorial Rink |
| January 22, 2020 | (2) Weymouth Wildcats at (3) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 25, 2020 | (1) Natick Red Hawks at (0) Weymouth Wildcats | Connell Memorial Rink |
| January 29, 2020 | (1) Walpole Timberwolves at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 01, 2020 | (5) Weymouth Wildcats at (3) Needham Rockets | Babson Skating Center |
| February 05, 2020 | (7) Weymouth Wildcats at (0) Newton North Tigers | John A. Ryan Arena |
| February 08, 2020 | (3) Milton Wildcats at (1) Weymouth Wildcats | Connell Memorial Rink |
| February 12, 2020 | (0) Weymouth Wildcats at (3) Braintree Wamps | Zapustas Arena |
| February 17, 2020 | (2) Weymouth Wildcats at (6) Arlington Spy Ponders | Ed Burns Arena |
| February 19, 2020 | (0) Weymouth Wildcats at (4) Franklin Panthers
COACH MELCHIONO SHOWDOWN |
Kennedy Memorial Skating Rink |
| February 20, 2020 | (5) Barnstable Red Hawks at (4) Weymouth Wildcats
COACH MELCHIONO SHOWDOWN |
Hyannis Youth and Community Center |
