| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2023 | (1) Lexington Minutemen at (5) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 16, 2023 | (7) Belmont Marauders at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 20, 2023 | (5) Woburn Tanners at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 27, 2023 | (1) Watertown/Wayland Raiders at (4) Waltham Hawks | Veterans Memorial Rink |
| December 30, 2023 | (5) Dover-Sherborn/Weston Raiders at (2) Watertown/Wayland Raiders
Plan Road Cup |
John A. Ryan Arena |
| January 03, 2024 | (1) Melrose Red Hawks at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 06, 2024 | (2) Watertown/Wayland Raiders at (4) Burlington Red Devils | Burlington Ice Palace |
| January 11, 2024 | (5) Watertown/Wayland Raiders at (3) Wilmington Wildcats | Breakaway Ice Center |
| January 13, 2024 | (3) Stoneham Spartans at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 17, 2024 | (2) Norwell Clippers at (6) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 20, 2024 | (2) Watertown/Wayland Raiders at (2) Wakefield Warriors
OT game ends in a tie |
Stoneham Arena |
| January 24, 2024 | (0) Watertown/Wayland Raiders at (5) Reading Rockets | Burbank Ice Arena |
| January 26, 2024 | (5) Winchester Red & Black at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 31, 2024 | (6) Arlington Spy Ponders at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 03, 2024 | (2) Watertown/Wayland Raiders at (3) Melrose Red Hawks | Kasabuski Arena |
| February 07, 2024 | (2) Burlington Red Devils at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 10, 2024 | (1) Wilmington Wildcats at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 14, 2024 | (4) Watertown/Wayland Raiders at (1) Stoneham Spartans | Stoneham Arena |
| February 17, 2024 | (2) Wakefield Warriors at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 22, 2024 | (7) Shawsheen Rams at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 28, 2024 | (7) Watertown/Wayland Raiders at (4) St. Paul Diocesan Knights
MIAA D3 BOYS STATE TOURNAMENT - Round 32 |
Worcester Ice Center |
| March 02, 2024 | (1) Watertown/Wayland Raiders at (6) Scituate Sailors
MIAA D3 BOYS STATE TOURNAMENT - Sweet 16 |
Hobomock Arena |
