| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) East Boston Jets at (8) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 14, 2019 | (3) Dedham Marauders at (2) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 18, 2019 | (0) Dover-Sherborn/Weston Raiders at (2) Holliston Panthers | Loring Arena |
| December 21, 2019 | (3) Hopedale/Millis Blue Raiders at (5) Dover-Sherborn/Weston Raiders
St. Joseph Prep Holiday Tourney |
Warrior Ice Arena |
| December 23, 2019 | (2) Dover-Sherborn/Weston Raiders at (6) Holliston Panthers
ST JOSEPH PREP HOLDIAY TOURNAMENT |
Warrior Ice Arena |
| December 28, 2019 | (7) Peabody/Salem Tanners at (4) Dover-Sherborn/Weston Raiders | Chase Arena |
| January 04, 2020 | (1) Dover-Sherborn/Weston Raiders at (7) Ashland Clockers | Loring Arena |
| January 08, 2020 | (4) Dover-Sherborn/Weston Raiders at (1) Northeast Tech Golden Knights | Valley Forum II |
| January 11, 2020 | (1) Dover-Sherborn/Weston Raiders at (8) Hopkinton Hillers | New England Sports Center |
| January 15, 2020 | (3) Dover-Sherborn/Weston Raiders at (5) Bellingham Blackhawks | Pirelli Veterans Arena |
| January 18, 2020 | (5) Westwood Wolverines at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 22, 2020 | (2) Norton Lancers at (4) Dover-Sherborn/Weston Raiders | Chase Arena |
| January 25, 2020 | (2) Dover-Sherborn/Weston Raiders at (5) Dedham Marauders | Noble & Greenough School |
| January 29, 2020 | (0) Dover-Sherborn/Weston Raiders at (4) Norwood Mustangs | Bajko Memorial Rink |
| February 01, 2020 | (0) Dover-Sherborn/Weston Raiders at (5) Medway Mustangs | Pirelli Veterans Arena |
| February 05, 2020 | (8) Medfield Warriors at (0) Dover-Sherborn/Weston Raiders | Chase Arena |
| February 12, 2020 | (4) Bellingham Blackhawks at (7) Dover-Sherborn/Weston Raiders | Chase Arena |
| February 15, 2020 | (3) Pembroke Titans at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 17, 2020 | (2) Wayland Warriors at (6) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 19, 2020 | (7) Medway Mustangs at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
