| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (6) Diman Bengals at (7) Apponequet/Old Colony Lakers
Prenda Cup |
Driscoll Arena |
| December 15, 2018 | (1) Durfee Hilltoppers at (5) Diman Bengals
Dartmouth Christmas Tournament |
Driscoll Arena |
| December 15, 2018 | (1) Durfee Hilltoppers at (5) Diman Bengals
Prenda Cup |
Driscoll Arena |
| December 19, 2018 | (0) Diman Bengals at (3) Greater New Bedford Vo-Tech Bears | Hetland Arena |
| December 22, 2018 | (5) Diman Bengals at (3) South Shore Voc-Tech Vikings | Rockland Arena |
| December 26, 2018 | (1) Blue Hills Warriors at (2) Diman Bengals | Driscoll Arena |
| December 29, 2018 | (0) Diman Bengals at (9) Upper Cape Tech Rams | Gallo Arena |
| January 02, 2019 | (7) Southeastern/Bristol-Plymouth Hawks at (1) Diman Bengals | Driscoll Arena |
| January 05, 2019 | (6) Diman Bengals at (0) Tri-County Cougars | Pirelli Veterans Arena |
| January 09, 2019 | (4) Sacred Heart Saints at (5) Diman Bengals | Driscoll Arena |
| January 12, 2019 | (2) Diman Bengals at (5) Cape Tech/Cape Cod Academy Crusaders | Charles Moore Arena |
| January 16, 2019 | (2) South Shore Voc-Tech Vikings at (7) Diman Bengals | Driscoll Arena |
| January 19, 2019 | (4) Diman Bengals at (3) Blue Hills Warriors | Zapustas Arena |
| January 21, 2019 | (6) Apponequet/Old Colony Lakers at (4) Diman Bengals | Driscoll Arena |
| January 23, 2019 | (2) Upper Cape Tech Rams at (6) Diman Bengals | Driscoll Arena |
| January 26, 2019 | (0) Diman Bengals at (8) Southeastern/Bristol-Plymouth Hawks | Raynham IcePlex |
| January 30, 2019 | (2) Tri-County Cougars at (5) Diman Bengals | Driscoll Arena |
| February 02, 2019 | (2) Diman Bengals at (6) Sacred Heart Saints | The Bog |
| February 06, 2019 | (6) Diman Bengals at (2) Durfee Hilltoppers | Driscoll Arena |
| February 09, 2019 | (3) Cape Tech/Cape Cod Academy Crusaders at (5) Diman Bengals | Driscoll Arena |
| February 16, 2019 | (5) Greater New Bedford Vo-Tech Bears at (2) Diman Bengals | Driscoll Arena |
| February 25, 2019 | (5) St. John Paul II Lions at (1) Diman Bengals | Driscoll Arena |
