| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (2) Watertown/Wayland Raiders at (2) Rockland Bulldogs | Rockland Arena |
| December 18, 2019 | (2) Bedford Bucs at (0) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 21, 2019 | (3) Lexington Minutemen at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| December 26, 2019 | (6) Watertown/Wayland Raiders at (0) Everett Crimson Tide
Everett Christmas Tournament |
Allied Veterans Rink |
| December 27, 2019 | (0) Northeast Tech Golden Knights at (3) Watertown/Wayland Raiders
Everett Christmas Tournament |
Allied Veterans Rink |
| December 31, 2019 | (1) Peabody/Salem Tanners at (5) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 04, 2020 | (0) Rockland Bulldogs at (4) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 08, 2020 | (0) Essex Tech Hawks at (2) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 11, 2020 | (7) Watertown/Wayland Raiders at (0) OBryant Tigers | John A. Ryan Arena |
| January 15, 2020 | (0) Watertown/Wayland Raiders at (3) Bedford Bucs | Edge Sports Center |
| January 18, 2020 | (2) Somerville Highlanders at (5) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 22, 2020 | (1) Wakefield Warriors at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 25, 2020 | (3) Watertown/Wayland Raiders at (6) Hopedale/Millis Blue Raiders | Blackstone Valley Ice Arena |
| January 29, 2020 | (0) Watertown/Wayland Raiders at (3) Newton South Lions | John A. Ryan Arena |
| February 01, 2020 | (7) Watertown/Wayland Raiders at (2) OBryant Tigers | Matthews Arena |
| February 05, 2020 | (8) Watertown/Wayland Raiders at (4) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| February 08, 2020 | (5) Watertown/Wayland Raiders at (1) Saugus Sachems | Kasabuski Arena |
| February 12, 2020 | (2) Newton South Lions at (3) Watertown/Wayland Raiders | John A. Ryan Arena |
| February 15, 2020 | (2) Watertown/Wayland Raiders at (0) Essex Tech Hawks | Essex Sports Center |
| February 20, 2020 | (0) Watertown/Wayland Raiders at (5) Wakefield Warriors | Stoneham Arena |
| February 27, 2020 | (1) Rockport Vikings at (3) Watertown/Wayland Raiders
Boys D3 N Playoffs |
O'Brien Arena |
| March 02, 2020 | (1) Watertown/Wayland Raiders at (2) Swampscott Big Blue
Boys D3N Playoff |
Stoneham Arena |
