| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Reading Rockets at (2) Wakefield Warriors | Burbank Ice Arena |
| December 18, 2019 | (4) Wakefield Warriors at (2) Lexington Minutemen | Hayden Ice Facility |
| December 21, 2019 | (1) Wakefield Warriors at (5) Arlington Spy Ponders | Ed Burns Arena |
| December 26, 2019 | (11) Wakefield Warriors at (1) Peabody/Salem Tanners
Kasabuski Holiday Tourney - First Round |
Kasabuski Arena |
| December 27, 2019 | (2) Wakefield Warriors at (1) North Reading Hornets
Kasabuski Holiday Classic |
Kasabuski Arena |
| December 30, 2019 | (7) Wakefield Warriors at (1) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| January 01, 2020 | (5) Burlington Red Devils at (2) Wakefield Warriors | Stoneham Arena |
| January 07, 2020 | (3) Wilmington Wildcats at (1) Wakefield Warriors | Stoneham Arena |
| January 11, 2020 | (4) Wakefield Warriors at (3) Melrose Red Hawks | Kasabuski Arena |
| January 15, 2020 | (1) Wakefield Warriors at (3) Stoneham Spartans | Stoneham Arena |
| January 18, 2020 | (0) Woburn Tanners at (5) Wakefield Warriors | Burbank Ice Arena |
| January 20, 2020 | (7) Melrose Red Hawks at (5) Wakefield Warriors | Stoneham Arena |
| January 22, 2020 | (1) Wakefield Warriors at (1) Watertown/Wayland Raiders | John A. Ryan Arena |
| January 25, 2020 | (3) Belmont Marauders at (0) Wakefield Warriors | Stoneham Arena |
| January 29, 2020 | (1) Winchester Red & Black at (3) Wakefield Warriors | Stoneham Arena |
| February 01, 2020 | (1) Wakefield Warriors at (1) Burlington Red Devils | Burlington Ice Palace |
| February 05, 2020 | (5) Wakefield Warriors at (2) Beverly Panthers | Raymond J. Bourque Arena |
| February 08, 2020 | (3) Wakefield Warriors at (3) Wilmington Wildcats | Ristuccia Memorial Arena |
| February 15, 2020 | (2) Stoneham Spartans at (3) Wakefield Warriors | Stoneham Arena |
| February 20, 2020 | (0) Watertown/Wayland Raiders at (5) Wakefield Warriors | Stoneham Arena |
| February 25, 2020 | (1) Wakefield Warriors at (5) Gloucester Fishermen
Boys D2 N Playoff |
Stoneham Arena |
