| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 7:40 PM | (1) Lexington Minutemen at (5) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 16, 2:20 PM | (7) Belmont Marauders at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 20, 8:00 PM | (5) Woburn Tanners at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 27, 7:00 PM | (1) Watertown/Wayland Raiders at (4) Waltham Hawks | Veterans Memorial Rink |
| Dec. 30, 4:00 PM | (5) Dover-Sherborn/Weston Raiders at (2) Watertown/Wayland Raiders
Plan Road Cup |
John A. Ryan Arena |
| Jan. 3, 8:00 PM | (1) Melrose Red Hawks at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 6, 2:00 PM | (2) Watertown/Wayland Raiders at (4) Burlington Red Devils | Burlington Ice Palace |
| Jan. 11, 7:15 PM | (5) Watertown/Wayland Raiders at (3) Wilmington Wildcats | Breakaway Ice Center |
| Jan. 13, 4:20 PM | (3) Stoneham Spartans at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 17, 7:40 PM | (2) Norwell Clippers at (6) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 20, 8:00 PM | (2) Watertown/Wayland Raiders at (2) Wakefield Warriors
OT game ends in a tie |
Stoneham Arena |
| Jan. 24, 7:45 PM | (0) Watertown/Wayland Raiders at (5) Reading Rockets | Burbank Ice Arena |
| Jan. 26, 7:50 PM | (5) Winchester Red & Black at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 31, 7:40 PM | (6) Arlington Spy Ponders at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 3, 5:00 PM | (2) Watertown/Wayland Raiders at (3) Melrose Red Hawks | Kasabuski Arena |
| Feb. 7, 4:00 PM | (2) Burlington Red Devils at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 10, 3:30 PM | (1) Wilmington Wildcats at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 14, 6:00 PM | (4) Watertown/Wayland Raiders at (1) Stoneham Spartans | Stoneham Arena |
| Feb. 17, 4:20 PM | (2) Wakefield Warriors at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 22, 6:00 PM | (7) Shawsheen Rams at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 28, 3:00 PM | (7) Watertown/Wayland Raiders at (4) St. Paul Diocesan Knights
MIAA D3 BOYS STATE TOURNAMENT - Round 32 |
Worcester Ice Center |
| Mar. 2, 4:40 PM | (1) Watertown/Wayland Raiders at (6) Scituate Sailors
MIAA D3 BOYS STATE TOURNAMENT - Sweet 16 |
Hobomock Arena |
