| Date & Time | Game | Venue |
|---|---|---|
| Dec. 12, 5:00 PM | (3) Hanover Hawks at (3) Dover-Sherborn/Weston Raiders
Gormley Cup (Hanover wins 4-3 double OT) |
Gallo Arena |
| Dec. 14, 4:30 PM | (2) Dover-Sherborn/Weston Raiders at (1) Sandwich Blue Knights
Gormley Cup |
Gallo Arena |
| Dec. 16, 8:30 PM | (6) Dover-Sherborn/Weston Raiders at (0) Bellingham Blackhawks | Pirelli Veterans Arena |
| Dec. 18, 7:00 PM | (0) Norton Lancers at (3) Dover-Sherborn/Weston Raiders | Rivers School |
| Dec. 21, 7:30 PM | (3) Dover-Sherborn/Weston Raiders at (4) Medway Mustangs | Pirelli Veterans Arena |
| Dec. 28, 4:00 PM | (6) Watertown/Wayland Raiders at (4) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 4, 6:30 PM | (2) Dover-Sherborn/Weston Raiders at (2) Lunenburg/Ayer-Shirley Blue Knights | Rivers School |
| Jan. 8, 6:00 PM | (2) Medfield Warriors at (0) Dover-Sherborn/Weston Raiders | Rivers School |
| Jan. 11, 2:00 PM | (3) Dover-Sherborn/Weston Raiders at (4) Westwood Wolverines | Canton Ice House |
| Jan. 17, 7:40 PM | (3) Dover-Sherborn/Weston Raiders at (2) Holliston Panthers | Pirelli Veterans Arena |
| Jan. 22, 8:00 PM | (5) Hopkinton Hillers at (3) Dover-Sherborn/Weston Raiders | Rivers School |
| Jan. 25, 6:45 PM | (1) Dover-Sherborn/Weston Raiders at (4) Dedham Marauders | Noble & Greenough School |
| Jan. 29, 7:00 PM | (1) Norwood Mustangs at (5) Dover-Sherborn/Weston Raiders | Rivers School |
| Feb. 1, 5:00 PM | (1) Bellingham Blackhawks at (7) Dover-Sherborn/Weston Raiders | Rivers School |
| Feb. 4, 7:30 PM | (1) Dover-Sherborn/Weston Raiders at (2) Medfield Warriors | Pirelli Veterans Arena |
| Feb. 5, 7:30 PM | (6) Dover-Sherborn/Weston Raiders at (0) Norton Lancers | Foxboro Sports Center |
| Feb. 7, 7:10 PM | (2) Medway Mustangs at (10) Dover-Sherborn/Weston Raiders | Rivers School |
| Feb. 15, 7:00 PM | (4) Dover-Sherborn/Weston Raiders at (2) Martha's Vineyard Vineyarders
Farleigh S. Dickinson Tournament |
Martha's Vineyard Arena |
| Feb. 16, 1:00 PM | (4) Dover-Sherborn/Weston Raiders at (6) Essex Tech Hawks
Farleigh Dickinson Tournament - Championship Game - BOYS |
Martha's Vineyard Arena |
| Feb. 17, 12:00 PM | (7) Dover-Sherborn/Weston Raiders at (2) Hudson Hawks | New England Sports Center |
| Feb. 19, 8:05 PM | (6) Dover-Sherborn/Weston Raiders at (0) Acton-Boxboro Revolution | Nashoba Valley Olympia |
| Feb. 27, 8:00 PM | (2) Mashpee/Monomoy Monarchs at (4) Dover-Sherborn/Weston Raiders
MIAA D4 BOYS STATE TOURNAMENT - Round 32 |
Rivers School |
| Mar. 2, 8:00 PM | (1) Northeast Tech Golden Knights at (4) Dover-Sherborn/Weston Raiders
MIAA D4 Boys State Tournament - Round of 16 |
Rivers School |
| Mar. 5, 5:00 PM | (2) Dedham Marauders at (0) Dover-Sherborn/Weston Raiders
MIAA D4 BOYS STATE TOURNAMENT - Round 8 |
Loring Arena |
