| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (0) OBryant Tigers at (4) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 17, 2018 | (4) Pentucket Panthers at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 19, 2018 | (2) Watertown/Wayland Raiders at (1) Saugus Sachems | Kasabuski Arena |
| December 22, 2018 | (4) Worcester (Burncoat) Wildcats at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 26, 2018 | (1) Watertown/Wayland Raiders at (4) Lynnfield Pioneers
WOLFPACK HOLIDAY TOURNAMENT |
Murphy Memorial Rink |
| December 27, 2018 | (2) Watertown/Wayland Raiders at (0) Latin Academy Dragons
Castle Island Tournament |
Murphy Memorial Rink |
| January 02, 2019 | (4) Wakefield Warriors at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 05, 2019 | (4) Watertown/Wayland Raiders at (1) Minuteman Mustangs | Valley Sports Arena |
| January 06, 2019 | (6) Watertown/Wayland Raiders at (0) OBryant Tigers | Matthews Arena |
| January 09, 2019 | (2) Watertown/Wayland Raiders at (2) Somerville Highlanders | Veterans Memorial Rink |
| January 12, 2019 | (4) Watertown/Wayland Raiders at (3) Essex Tech Hawks | Essex Sports Center |
| January 14, 2019 | (2) Dover-Sherborn/Weston Raiders at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 19, 2019 | (1) Essex Tech Hawks at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 23, 2019 | (1) Bedford Bucs at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 30, 2019 | (2) Watertown/Wayland Raiders at (2) Newton South Lions | John A. Ryan Arena |
| February 02, 2019 | (3) Watertown/Wayland Raiders at (1) Hopedale / Milford Blue Raiders | Blackstone Valley Ice Arena |
| February 06, 2019 | (1) Watertown/Wayland Raiders at (3) Wakefield Warriors | Stoneham Arena |
| February 13, 2019 | (2) Watertown/Wayland Raiders at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 16, 2019 | (1) Watertown/Wayland Raiders at (3) Bedford Bucs | Edge Sports Center |
| February 20, 2019 | (4) Newton South Lions at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 28, 2019 | (4) Watertown/Wayland Raiders at (1) Wayland Warriors | John A. Ryan Arena |
| March 02, 2019 | (2) Watertown/Wayland Raiders at (3) Dracut/Tyngsboro Middies | Chelmsford Forum |
