| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (3) Durfee Hilltoppers at (7) Diman Bengals | Driscoll Arena |
| December 21, 2019 | (4) Somerset Berkley Raiders at (0) Diman Bengals
Prenda Cup (day 2) |
Driscoll Arena |
| December 23, 2019 | (7) Greater New Bedford Vo-Tech Bears at (0) Diman Bengals | Driscoll Arena |
| December 28, 2019 | (4) Tri-County Cougars at (4) Diman Bengals | Driscoll Arena |
| December 30, 2019 | (0) Diman Bengals at (4) Upper Cape Tech Rams | Gallo Arena |
| January 04, 2020 | (4) Sacred Heart Saints at (6) Diman Bengals | Driscoll Arena |
| January 06, 2020 | (9) Diman Bengals at (4) Durfee Hilltoppers | Driscoll Arena |
| January 08, 2020 | (4) Coyle & Cassidy Warriors at (3) Diman Bengals | Driscoll Arena |
| January 11, 2020 | (4) Diman Bengals at (4) South Shore Voc-Tech Vikings | Rockland Arena |
| January 15, 2020 | (4) Southeastern/Bristol-Plymouth Hawks at (2) Diman Bengals | Driscoll Arena |
| January 18, 2020 | (4) Upper Cape Tech Rams at (1) Diman Bengals | Driscoll Arena |
| January 22, 2020 | (7) Blue Hills Warriors at (3) Diman Bengals | Driscoll Arena |
| January 25, 2020 | (5) Diman Bengals at (3) Tri-County Cougars | Pirelli Veterans Arena |
| January 29, 2020 | (3) Diman Bengals at (3) Sacred Heart Saints | The Bog |
| February 03, 2020 | (2) Durfee Hilltoppers at (4) Diman Bengals | Driscoll Arena |
| February 05, 2020 | (0) South Shore Voc-Tech Vikings at (0) Diman Bengals | Driscoll Arena |
| February 08, 2020 | (1) Diman Bengals at (10) Southeastern/Bristol-Plymouth Hawks | Raynham IcePlex |
| February 10, 2020 | (1) Diman Bengals at (7) Greater New Bedford Vo-Tech Bears | Hetland Arena |
| February 11, 2020 | (1) Diman Bengals at (3) Blue Hills Warriors | Canton Ice House |
| February 12, 2020 | (5) Diman Bengals at (8) Apponequet/Old Colony Lakers | Driscoll Arena |
