| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (1) Bellingham Blackhawks at (4) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 15, 2018 | (2) Norton Lancers at (5) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 19, 2018 | (0) Dover-Sherborn/Weston Raiders at (1) Dedham Marauders | Noble & Greenough School |
| December 22, 2018 | (2) Holliston Panthers at (2) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 26, 2018 | (3) Shawsheen Rams at (3) Dover-Sherborn/Weston Raiders
Hillies Christmas Classic |
Veterans Memorial Ice Rink |
| December 28, 2018 | (0) Dover-Sherborn/Weston Raiders at (4) North Andover Scarlet Knights
Hillies Hockey Christmas Tournament - Guptill |
Veterans Memorial Ice Rink |
| January 05, 2019 | (1) Dover-Sherborn/Weston Raiders at (2) Medway Mustangs | Pirelli Veterans Arena |
| January 09, 2019 | (4) Ashland Clockers at (0) Dover-Sherborn/Weston Raiders | Chase Arena |
| January 14, 2019 | (2) Dover-Sherborn/Weston Raiders at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 16, 2019 | (5) Hopkinton Hillers at (0) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 23, 2019 | (2) Dover-Sherborn/Weston Raiders at (3) Westwood Wolverines | Canton Ice House |
| January 26, 2019 | (4) Dover-Sherborn/Weston Raiders at (2) Norton Lancers | Foxboro Sports Center |
| January 30, 2019 | (0) Dedham Marauders at (3) Dover-Sherborn/Weston Raiders | Chase Arena |
| February 02, 2019 | (3) Norwood Mustangs at (0) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 04, 2019 | (3) Northeast Tech Golden Knights at (6) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 06, 2019 | (1) Medway Mustangs at (3) Dover-Sherborn/Weston Raiders | Chase Arena |
| February 09, 2019 | (2) Dover-Sherborn/Weston Raiders at (4) Medfield Warriors | Pirelli Veterans Arena |
| February 13, 2019 | (2) Watertown/Wayland Raiders at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 16, 2019 | (1) Dover-Sherborn/Weston Raiders at (3) Bellingham Blackhawks | Pirelli Veterans Arena |
| February 18, 2019 | (6) Wayland Warriors at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
