| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (2) Watertown Raiders at (6) Reading Rockets | Burbank Ice Arena |
| December 15, 2018 | (6) Winchester Red & Black at (3) Watertown Raiders | John A. Ryan Arena |
| December 19, 2018 | (0) Watertown Raiders at (6) Arlington Spy Ponders | Ed Burns Arena |
| December 22, 2018 | (5) Stoneham Spartans at (2) Watertown Raiders | John A. Ryan Arena |
| December 31, 2018 | (3) Winthrop Vikings at (1) Watertown Raiders | John A. Ryan Arena |
| January 02, 2019 | (0) Watertown Raiders at (3) Winthrop Vikings | Larsen Rink |
| January 05, 2019 | (2) Watertown Raiders at (7) Wakefield Warriors | Stoneham Arena |
| January 09, 2019 | (6) Melrose Red Hawks at (1) Watertown Raiders | John A. Ryan Arena |
| January 12, 2019 | (2) Burlington Red Devils at (6) Watertown Raiders | John A. Ryan Arena |
| January 16, 2019 | (2) Wilmington Wildcats at (2) Watertown Raiders | John A. Ryan Arena |
| January 19, 2019 | (3) Lexington Minutemen at (2) Watertown Raiders | John A. Ryan Arena |
| January 21, 2019 | (2) Watertown Raiders at (6) Medford/Malden Mustangs | LoConte Rink |
| January 26, 2019 | (7) Belmont/Watertown Marauders at (0) Watertown Raiders | John A. Ryan Arena |
| January 30, 2019 | (7) Woburn Tanners at (0) Watertown Raiders | John A. Ryan Arena |
| February 02, 2019 | (1) Watertown Raiders at (6) Stoneham Spartans | Stoneham Arena |
| February 06, 2019 | (6) Wakefield Warriors at (2) Watertown Raiders | John A. Ryan Arena |
| February 09, 2019 | (7) Melrose Red Hawks at (1) Watertown Raiders | Flynn Memorial Rink |
| February 11, 2019 | (4) Medford/Malden Mustangs at (2) Watertown Raiders | John A. Ryan Arena |
| February 13, 2019 | (7) Watertown Raiders at (4) Burlington Red Devils | Burlington Ice Palace |
| February 16, 2019 | (1) Watertown Raiders at (5) Wilmington Wildcats | Ristuccia Memorial Arena |
