| Date & Time | Game | Venue |
|---|---|---|
| December 18, 2019 | (3) Falmouth Clippers at (1) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| December 21, 2019 | (1) Bridgewater-Raynham Trojans at (2) Shrewsbury Colonials | NorthStar Ice Sports |
| December 23, 2019 | (0) Pembroke Titans at (7) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| December 27, 2019 | (2) Bridgewater-Raynham Trojans at (6) Duxbury Dragons
Oyster Cup Holiday Tournament |
The Bog |
| December 28, 2019 | (4) Barnstable Red Hawks at (0) Bridgewater-Raynham Trojans
Island Creek Oysters Cup Consolation Game |
The Bog |
| January 01, 2020 | (6) Bridgewater-Raynham Trojans at (6) Coyle & Cassidy Warriors | Raynham IcePlex |
| January 04, 2020 | (1) Dartmouth Indians at (4) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 08, 2020 | (3) King Philip Warriors at (0) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 11, 2020 | (0) Oliver Ames Tigers at (4) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 15, 2020 | (0) Durfee Hilltoppers at (10) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 20, 2020 | (2) Bridgewater-Raynham Trojans at (1) Pembroke Titans | Hobomock Arena |
| January 22, 2020 | (2) Weymouth Wildcats at (3) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| January 25, 2020 | (13) Bridgewater-Raynham Trojans at (1) Durfee Hilltoppers | Driscoll Arena |
| January 29, 2020 | (2) Bridgewater-Raynham Trojans at (2) Dartmouth Indians | Hetland Arena |
| February 01, 2020 | (2) Silver Lake Lakers at (3) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| February 05, 2020 | (4) Bridgewater-Raynham Trojans at (0) Stoughton/Brockton Knight Boxers | Asiaf Skating Arena |
| February 08, 2020 | (3) Bridgewater-Raynham Trojans at (1) Walpole Timberwolves | Noble & Greenough School |
| February 10, 2020 | (2) Bridgewater-Raynham Trojans at (3) Acton-Boxboro Revolution | Nashoba Valley Olympia |
| February 12, 2020 | (1) Stoughton/Brockton Knight Boxers at (7) Bridgewater-Raynham Trojans | Bridgewater Ice Arena |
| February 15, 2020 | (3) Bridgewater-Raynham Trojans at (2) Milton Wildcats | Ulin Memorial Rink |
| February 26, 2020 | (2) Archbishop Williams Bishops at (1) Bridgewater-Raynham Trojans
Boys D1 S Playoff |
Gallo Arena |
