| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (0) Tri-County Cougars at (6) Foxboro Warriors | Foxboro Sports Center |
| December 15, 2018 | (2) Tri-County Cougars at (7) Greater Lowell/Nashoba Tech Vikings | Chelmsford Forum |
| December 19, 2018 | (5) Blue Hills Warriors at (6) Tri-County Cougars | Pirelli Veterans Arena |
| December 22, 2018 | (0) Tri-County Cougars at (4) Southeastern/Bristol-Plymouth Hawks | Raynham IcePlex |
| December 26, 2018 | (0) Tri-County Cougars at (7) Bellingham Blackhawks
Bellingham Christmas Tournament |
Pirelli Veterans Arena |
| December 27, 2018 | (3) Tri-County Cougars at (5) Stoughton/Brockton Knight Boxers
Bellingham Christmas Tournament |
Pirelli Veterans Arena |
| December 29, 2018 | (4) Tri-County Cougars at (1) South Shore Voc-Tech Vikings | Rockland Arena |
| January 02, 2019 | (8) Upper Cape Tech Rams at (2) Tri-County Cougars | Pirelli Veterans Arena |
| January 04, 2019 | (6) Tri-County Cougars at (2) OBryant Tigers | Matthews Arena |
| January 05, 2019 | (6) Diman Bengals at (0) Tri-County Cougars | Pirelli Veterans Arena |
| January 07, 2019 | (2) Sacred Heart Saints at (4) Tri-County Cougars | Pirelli Veterans Arena |
| January 12, 2019 | (4) Tri-County Cougars at (3) Blue Hills Warriors | Zapustas Arena |
| January 14, 2019 | (3) Greater Lowell/Nashoba Tech Vikings at (5) Tri-County Cougars | Pirelli Veterans Arena |
| January 17, 2019 | (9) Southeastern/Bristol-Plymouth Hawks at (0) Tri-County Cougars | Pirelli Veterans Arena |
| January 19, 2019 | (1) Tri-County Cougars at (6) Sacred Heart Saints | The Bog |
| January 23, 2019 | (2) South Shore Voc-Tech Vikings at (6) Tri-County Cougars | Pirelli Veterans Arena |
| January 26, 2019 | (4) Tri-County Cougars at (9) Upper Cape Tech Rams | Gallo Arena |
| January 30, 2019 | (2) Tri-County Cougars at (5) Diman Bengals | Driscoll Arena |
| February 06, 2019 | (8) Foxboro Warriors at (2) Tri-County Cougars | Pirelli Veterans Arena |
