| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (0) St. Joseph Prep/Mount Alvernia The Phoenix at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 12, 2018 | (6) St. Peter Marian Guardians at (0) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 15, 2018 | (5) Norwood Mustangs at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 17, 2018 | (1) Cambridge Rindge & Latin Falcons at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 19, 2018 | (7) Westwood Wolverines at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 02, 2019 | (4) Medfield Warriors at (0) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 05, 2019 | (1) Dover-Sherborn/Hopkinton Raiders at (4) Dedham Marauders | Noble & Greenough School |
| January 07, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (4) Medway/Ashland Mustangs | New England Sports Center |
| January 16, 2019 | (9) Dover-Sherborn/Hopkinton Raiders at (2) Shawsheen/Bedford Rams | Janas Memorial Rink |
| January 28, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (4) St. Peter Marian Guardians | Worcester Ice Center |
| January 30, 2019 | (1) Dover-Sherborn/Hopkinton Raiders at (9) Norwood Mustangs | Bajko Memorial Rink |
| February 02, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (5) Westwood Wolverines | Canton Ice House |
| February 09, 2019 | (5) Dedham Marauders at (1) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| February 13, 2019 | (4) Medway/Ashland Mustangs at (0) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| February 14, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (3) Cambridge Rindge & Latin Falcons | Simoni Skating Rink |
| February 16, 2019 | (1) Shawsheen/Bedford Rams at (5) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| February 18, 2019 | (1) Dover-Sherborn/Hopkinton Raiders at (4) Medfield Warriors | Rodman Arena |
| February 20, 2019 | (4) Dover-Sherborn/Hopkinton Raiders at (3) St. Joseph Prep/Mount Alvernia The Phoenix | Warrior Ice Arena |
| February 22, 2019 | (0) Dover-Sherborn/Hopkinton Raiders at (5) Old Rochester Bulldogs
rescheduled from 1-20 |
Travis Roy Arena |
