| Date & Time | Game | Venue |
|---|---|---|
| December 11, 2018 | (4) Wakefield Warriors at (4) Winchester Red & Black | O'Brien Arena |
| December 15, 2018 | (4) Reading Rockets at (1) Wakefield Warriors | Burbank Ice Arena |
| December 19, 2018 | (2) Wakefield Warriors at (1) Lexington Minutemen | Edge Sports Center |
| December 22, 2018 | (9) Wakefield Warriors at (3) Burlington Red Devils | Burlington Ice Palace |
| December 30, 2018 | (7) Wakefield Warriors at (8) Beverly/Danvers/Ipswich Panthers | Raymond J. Bourque Arena |
| January 01, 2019 | (2) Stoneham Spartans at (0) Wakefield Warriors | Stoneham Arena |
| January 05, 2019 | (2) Watertown Raiders at (7) Wakefield Warriors | Stoneham Arena |
| January 08, 2019 | (2) Wakefield Warriors at (1) Wilmington Wildcats | Ristuccia Memorial Arena |
| January 12, 2019 | (4) Melrose Red Hawks at (2) Wakefield Warriors | Ristuccia Memorial Arena |
| January 16, 2019 | (4) Wakefield Warriors at (2) Marblehead Magicians | O'Keefe Athletic Center Salem State |
| January 18, 2019 | (3) Arlington Spy Ponders at (1) Wakefield Warriors | Stoneham Arena |
| January 21, 2019 | (4) Beverly/Danvers/Ipswich Panthers at (1) Wakefield Warriors | Stoneham Arena |
| January 26, 2019 | (0) Wakefield Warriors at (2) Woburn Tanners | O'Brien Arena |
| January 30, 2019 | (3) Wakefield Warriors at (4) Belmont/Watertown Marauders | Skip Viglirolo Rink |
| February 02, 2019 | (2) Burlington Red Devils at (4) Wakefield Warriors | Burlington Ice Palace |
| February 06, 2019 | (6) Wakefield Warriors at (2) Watertown Raiders | John A. Ryan Arena |
| February 09, 2019 | (1) Wilmington Wildcats at (1) Wakefield Warriors | Ristuccia Memorial Arena |
| February 13, 2019 | (1) Wakefield Warriors at (6) Melrose Red Hawks | Flynn Memorial Rink |
| February 16, 2019 | (2) Wakefield Warriors at (6) Stoneham Spartans | Stoneham Arena |
| February 19, 2019 | (8) Marblehead Magicians at (5) Wakefield Warriors | Stoneham Arena |
