| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (8) Westwood Wolverines | Canton Ice House |
| December 16, 2019 | (1) Dover-Sherborn/Hopkinton Raiders at (2) Cambridge Rindge & Latin Falcons | Blackstone Valley Ice Arena |
| December 18, 2019 | (4) Medfield Warriors at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 21, 2019 | (6) Dedham Marauders at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 23, 2019 | (5) Masconomet Chieftains at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 28, 2019 | (5) Ursuline Academy Bears at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 30, 2019 | (2) Dover-Sherborn/Hopkinton Raiders at (8) Norwell | The Bog |
| January 03, 2020 | (6) Norwell at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 04, 2020 | (1) Medway/Ashland Mustangs at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 08, 2020 | (2) Dover-Sherborn/Hopkinton Raiders at (2) Norwood Mustangs | Bajko Memorial Rink |
| January 11, 2020 | (1) Dover-Sherborn/Hopkinton Raiders at (1) Masconomet Chieftains | Haverhill Valley Forum |
| January 14, 2020 | (2) Dover-Sherborn/Hopkinton Raiders at (2) Ursuline Academy Bears | Jim Roche Community Arena |
| January 18, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (3) Cambridge Rindge & Latin Falcons | Simoni Skating Rink |
| January 23, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (4) St. Peter Marian Guardians | Worcester Ice Center |
| January 25, 2020 | (5) St. Peter Marian Guardians at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 29, 2020 | (3) Westwood Wolverines at (0) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| February 01, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (2) Medfield Warriors | Boch Ice Center |
| February 08, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (3) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| February 12, 2020 | (3) Norwood Mustangs at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| February 15, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (3) Dedham Marauders | Noble & Greenough School |
