| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (5) Winchester Red & Black at (1) Watertown Raiders | John A. Ryan Arena |
| December 18, 2019 | (1) Watertown Raiders at (9) Arlington Spy Ponders | Ed Burns Arena |
| December 21, 2019 | (1) Watertown Raiders at (4) Lexington Minutemen | Hayden Ice Facility |
| January 01, 2020 | (5) Watertown Raiders at (3) Stoneham Spartans | Stoneham Arena |
| January 04, 2020 | (1) Wakefield Warriors at (0) Watertown Raiders | John A. Ryan Arena |
| January 08, 2020 | (2) Medford/Malden Mustangs at (0) Watertown Raiders | John A. Ryan Arena |
| January 11, 2020 | (3) Watertown Raiders at (3) Burlington Red Devils | Burlington Ice Palace |
| January 15, 2020 | (0) Watertown Raiders at (3) Wilmington Wildcats | Ristuccia Memorial Arena |
| January 18, 2020 | (0) Watertown Raiders at (6) Belmont/Watertown Marauders | Skip Viglirolo Rink |
| January 20, 2020 | (0) Watertown Raiders at (0) Medford/Malden Mustangs | LoConte Rink |
| January 22, 2020 | (2) Weymouth Wildcats at (5) Watertown Raiders | John A. Ryan Arena |
| January 25, 2020 | (1) Watertown Raiders at (8) Woburn Tanners | O'Brien Arena |
| January 27, 2020 | (0) Watertown Raiders at (0) Cambridge Rindge & Latin Falcons | Simoni Skating Rink |
| January 29, 2020 | (1) Watertown Raiders at (5) Reading Rockets | Essex Sports Center |
| February 01, 2020 | (2) Stoneham Spartans at (3) Watertown Raiders | John A. Ryan Arena |
| February 04, 2020 | (3) Watertown Raiders at (2) Wakefield Warriors | Stoneham Arena |
| February 10, 2020 | (0) Cambridge Rindge & Latin Falcons at (3) Watertown Raiders | John A. Ryan Arena |
| February 12, 2020 | (2) Burlington Red Devils at (1) Watertown Raiders | John A. Ryan Arena |
| February 15, 2020 | (1) Wilmington Wildcats at (3) Watertown Raiders | John A. Ryan Arena |
| February 17, 2020 | (8) Waltham Hawks at (2) Watertown Raiders | John A. Ryan Arena |
