| Date & Time | Game | Venue |
|---|---|---|
| Dec. 13, 3:00 PM | (1) Watertown/Wayland Raiders at (4) Belmont Marauders | Skip Viglirolo Rink |
| Dec. 17, 4:00 PM | (4) Woburn Tanners at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 20, 7:00 PM | (1) Watertown/Wayland Raiders at (7) Reading Rockets | Burbank Ice Arena |
| Dec. 23, 6:00 PM | (0) Somerville Highlanders at (4) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 27, 1:00 PM | (2) Newton South Lions at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| Dec. 27, 1:00 PM | (2) Newton South at (1) Watertown/Wayland Raiders
Raiders Holiday Cup |
John A. Ryan Arena |
| Dec. 30, 1:00 PM | (5) Newton North Tigers at (2) Watertown/Wayland Raiders
Raiders Holiday Cup |
John A. Ryan Arena |
| Jan. 3, 2:15 PM | (3) Watertown/Wayland Raiders at (10) Burlington Red Devils | Burlington Ice Palace |
| Jan. 7, 7:15 PM | (1) Watertown/Wayland Raiders at (3) Wilmington Wildcats | Breakaway Ice Center |
| Jan. 10, 4:30 PM | Stoneham Spartans at Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 13, 6:00 PM | Watertown/Wayland Raiders at Wakefield Warriors | Stoneham Arena |
| Jan. 17, 12:20 PM | Melrose Red Hawks at Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 21, 4:00 PM | Winchester Red & Black at Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 24, 4:20 PM | Arlington Spy Ponders at Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 28, 4:00 PM | Lexington Minutemen at Watertown/Wayland Raiders | John A. Ryan Arena |
| Jan. 31, 4:20 PM | Burlington Red Devils at Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 4, 5:45 PM | Wilmington Wildcats at Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 7, 4:00 PM | Watertown/Wayland Raiders at Stoneham Spartans | Stoneham Arena |
| Feb. 11, 7:45 PM | Wakefield Warriors at Watertown/Wayland Raiders | John A. Ryan Arena |
| Feb. 14, 7:30 PM | Watertown/Wayland Raiders at Melrose Red Hawks | Kasabuski Arena |
| Feb. 18, 5:45 PM | Dover-Sherborn/Weston Raiders at Watertown/Wayland Raiders
Post Road Cup |
John A. Ryan Arena |
