| Date & Time | Game | Venue |
|---|---|---|
| Dec. 9, 2:00 PM | (2) Dover-Sherborn/Weston Raiders at (0) Dennis-Yarmouth Dolphins | Tony Kent Arena |
| Dec. 13, 5:45 PM | (1) Dover-Sherborn/Weston Raiders at (2) Dedham Marauders | Bliss Omni and Flood Rink |
| Dec. 16, 8:30 PM | (0) Bellingham Blackhawks at (8) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Dec. 20, 6:00 PM | (5) Dover-Sherborn/Weston Raiders at (3) Norton Lancers | Foxboro Sports Center |
| Dec. 30, 4:00 PM | (5) Dover-Sherborn/Weston Raiders at (2) Watertown/Wayland Raiders
Plan Road Cup |
John A. Ryan Arena |
| Jan. 3, 8:30 PM | (2) Medway Mustangs at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 6, 7:30 PM | (1) Littleton/Bromfield Tigers at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 10, 5:00 PM | (2) Dover-Sherborn/Weston Raiders at (1) Norwood Mustangs | The Skating Club of Boston |
| Jan. 13, 4:00 PM | (3) Westwood Wolverines at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 17, 3:45 PM | (5) Dover-Sherborn/Weston Raiders at (2) Ashland Clockers | Loring Arena |
| Jan. 20, 6:00 PM | (0) Holliston Panthers at (5) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 24, 6:00 PM | (4) Dover-Sherborn/Weston Raiders at (2) Hopkinton Hillers | New England Sports Center |
| Jan. 27, 4:00 PM | (4) Medfield Warriors at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Jan. 29, 7:00 PM | (1) Norton Lancers at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Feb. 3, 5:30 PM | (10) Dover-Sherborn/Weston Raiders at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| Feb. 5, 8:10 PM | (2) Dedham Marauders at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Feb. 10, 4:30 PM | (2) Dover-Sherborn/Weston Raiders at (1) Medway Mustangs | Pirelli Veterans Arena |
| Feb. 12, 7:00 PM | (1) Hopedale/Millis Blue Raiders at (4) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Feb. 14, 8:30 PM | (2) Groton-Dunstable Crusaders at (7) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Feb. 17, 6:00 PM | (0) Dracut/Tyngsboro Middies at (6) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| Feb. 28, 8:00 PM | (1) Latin Academy Dragons at (6) Dover-Sherborn/Weston Raiders
MIAA D4 Boys State Tournament - Round 32 |
MacDowell Ice Arena |
| Mar. 2, 6:30 PM | (4) Dover-Sherborn/Weston Raiders at (1) Dedham Marauders
MIAA D4 BOYS STATE TOURNAMENT - Sweet 16 |
MacDowell Ice Arena |
| Mar. 6, 5:00 PM | (2) Dover-Sherborn/Weston Raiders at (1) Sandwich Blue Knights
MIAA D4 BOYS STATE TOURNAMENT - Elite 8 |
Stoneham Arena |
| Mar. 9, 3:00 PM | (2) Dover-Sherborn/Weston Raiders at (1) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Final 4 (2OT shootout) |
Gallo Arena |
| Mar. 17, 11:00 AM | (1) Hanover Hawks at (5) Dover-Sherborn/Weston Raiders
MIAA D4 BOYS STATE TOURNAMENT - State Championship |
TD Garden |
