| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2019 | (7) Tri-County Cougars at (4) OBryant Tigers | Matthews Arena |
| December 18, 2019 | (3) Tri-County Cougars at (5) South Shore Voc-Tech Vikings | Rockland Arena |
| December 21, 2019 | (0) Sacred Heart Saints at (5) Tri-County Cougars | Pirelli Veterans Arena |
| December 23, 2019 | (8) Nashoba Wolves at (0) Tri-County Cougars | Pirelli Veterans Arena |
| December 26, 2019 | (6) Stoughton Black Knights at (3) Tri-County Cougars
Bellingham Hockey Tournament |
Pirelli Veterans Arena |
| December 28, 2019 | (4) Tri-County Cougars at (4) Diman Bengals | Driscoll Arena |
| January 04, 2020 | (4) Southeastern/Bristol-Plymouth Hawks at (0) Tri-County Cougars | Pirelli Veterans Arena |
| January 06, 2020 | (1) OBryant Tigers at (7) Tri-County Cougars | Pirelli Veterans Arena |
| January 08, 2020 | (4) Tri-County Cougars at (2) Upper Cape Tech Rams | Gallo Arena |
| January 13, 2020 | (0) Tri-County Cougars at (5) Norton Lancers | Foxboro Sports Center |
| January 18, 2020 | (1) South Shore Voc-Tech Vikings at (5) Tri-County Cougars | Pirelli Veterans Arena |
| January 22, 2020 | (2) Tri-County Cougars at (4) Sacred Heart Saints | The Bog |
| January 25, 2020 | (5) Diman Bengals at (3) Tri-County Cougars | Pirelli Veterans Arena |
| January 29, 2020 | (0) Tri-County Cougars at (7) Southeastern/Bristol-Plymouth Hawks | Raynham IcePlex |
| February 01, 2020 | (5) Upper Cape Tech Rams at (1) Tri-County Cougars | Pirelli Veterans Arena |
| February 03, 2020 | (3) Norton Lancers at (2) Tri-County Cougars | Pirelli Veterans Arena |
| February 05, 2020 | (0) Tri-County Cougars at (6) Blue Hills Warriors | Canton Ice House |
| February 05, 2020 | (3) Blue Hills Warriors at (6) Tri-County Cougars
game suspended in third period due to bad ice. Tri-county leads 6-2 |
Pirelli Veterans Arena |
