| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2019 | (7) Tri-County Cougars at (4) OBryant Tigers | Matthews Arena |
| December 22, 2019 | (0) OBryant Tigers at (6) Latin Academy Dragons | Matthews Arena |
| December 26, 2019 | (0) OBryant Tigers at (6) Dedham Marauders
East Boton Deep Freeze |
Lt. Porrazzo Memorial Rink |
| December 27, 2019 | (7) OBryant Tigers at (2) East Boston Jets
EAST BOSTON DEEP FREEZE TOURNAMENT |
Lt. Porrazzo Memorial Rink |
| December 28, 2019 | (0) OBryant Tigers at (11) St. John Paul II Lions | Hyannis Youth and Community Center |
| January 06, 2020 | (1) OBryant Tigers at (7) Tri-County Cougars | Pirelli Veterans Arena |
| January 08, 2020 | (3) OBryant Tigers at (8) Everett Crimson Tide | Allied Veterans Rink |
| January 11, 2020 | (7) Watertown/Wayland Raiders at (0) OBryant Tigers | John A. Ryan Arena |
| January 19, 2020 | (3) Dighton-Rehoboth/Seekonk Falcons at (1) OBryant Tigers | Matthews Arena |
| January 22, 2020 | (5) OBryant Tigers at (12) Everett Crimson Tide | Allied Veterans Rink |
| January 30, 2020 | (0) East Boston Jets at (8) OBryant Tigers | Matthews Arena |
| February 01, 2020 | (7) Watertown/Wayland Raiders at (2) OBryant Tigers | Matthews Arena |
| February 03, 2020 | (5) Hamilton-Wenham Generals at (1) OBryant Tigers | Matthews Arena |
| February 07, 2020 | (4) Latin Academy Dragons at (2) OBryant Tigers | Matthews Arena |
| February 08, 2020 | (3) OBryant Tigers at (6) Durfee Hilltoppers | Driscoll Arena |
| February 11, 2020 | (7) St. John Paul II Lions at (1) OBryant Tigers | Matthews Arena |
| February 12, 2020 | (2) Durfee Hilltoppers at (7) OBryant Tigers | Matthews Arena |
| February 15, 2020 | (2) OBryant Tigers at (9) Dighton-Rehoboth/Seekonk Falcons | New England Sports Village |
| February 18, 2020 | (7) Latin Academy Dragons at (0) OBryant Tigers | Matthews Arena |
| February 19, 2020 | (2) OBryant Tigers at (10) Hamilton-Wenham Generals | Johnson Hockey Rink |
