| Date & Time | Game | Venue |
|---|---|---|
| December 09, 2023 | (2) Dover-Sherborn/Weston Raiders at (0) Dennis-Yarmouth, CC Tech, CC Academy Dolphins | Tony Kent Arena |
| December 13, 2023 | (1) Dover-Sherborn/Weston Raiders at (2) Dedham Marauders | Bliss Omni and Flood Rink |
| December 16, 2023 | (0) Bellingham Blackhawks at (8) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| December 20, 2023 | (5) Dover-Sherborn/Weston Raiders at (3) Norton Lancers | Foxboro Sports Center |
| December 30, 2023 | (5) Dover-Sherborn/Weston Raiders at (2) Watertown/Wayland Raiders
Plan Road Cup |
John A. Ryan Arena |
| January 03, 2024 | (2) Medway Mustangs at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 06, 2024 | (1) Littleton/Bromfield Tigers at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 10, 2024 | (2) Dover-Sherborn/Weston Raiders at (1) Norwood Mustangs | The Skating Club of Boston |
| January 13, 2024 | (3) Westwood Wolverines at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 17, 2024 | (5) Dover-Sherborn/Weston Raiders at (2) Ashland Clockers | Loring Arena |
| January 20, 2024 | (0) Holliston Panthers at (5) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 24, 2024 | (4) Dover-Sherborn/Weston Raiders at (2) Hopkinton Hillers | New England Sports Center |
| January 27, 2024 | (4) Medfield Warriors at (3) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 29, 2024 | (1) Norton Lancers at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 03, 2024 | (10) Dover-Sherborn/Weston Raiders at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| February 05, 2024 | (2) Dedham Marauders at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 10, 2024 | (2) Dover-Sherborn/Weston Raiders at (1) Medway Mustangs | Pirelli Veterans Arena |
| February 12, 2024 | (1) Hopedale / Milford Blue Raiders at (4) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 14, 2024 | (2) Groton-Dunstable Crusaders at (7) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 17, 2024 | (0) Dracut/Tyngsboro Middies at (6) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 28, 2024 | (1) Latin Academy Dragons at (6) Dover-Sherborn/Weston Raiders
MIAA D4 Boys State Tournament - Round 32 |
MacDowell Ice Arena |
| March 02, 2024 | (4) Dover-Sherborn/Weston Raiders at (1) Dedham Marauders
MIAA D4 BOYS STATE TOURNAMENT - Sweet 16 |
MacDowell Ice Arena |
| March 06, 2024 | (2) Dover-Sherborn/Weston Raiders at (1) Sandwich Blue Knights
MIAA D4 BOYS STATE TOURNAMENT - Elite 8 |
Stoneham Arena |
| March 09, 2024 | (2) Dover-Sherborn/Weston Raiders at (1) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Final 4 (2OT shootout) |
Gallo Arena |
| March 17, 2024 | (1) Hanover Hawks at (5) Dover-Sherborn/Weston Raiders
MIAA D4 BOYS STATE TOURNAMENT - State Championship |
TD Garden |
