| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (5) Wilmington Wildcats at (2) Woburn Tanners | O'Brien Arena |
| December 15, 2018 | (6) Woburn Tanners at (4) Burlington Red Devils | Burlington Ice Palace |
| December 19, 2018 | (6) Melrose Red Hawks at (1) Woburn Tanners | O'Brien Arena |
| December 21, 2018 | (1) Woburn Tanners at (2) Waltham Hawks
Jake and Joe's Holiday Tournament |
Veterans Memorial Rink |
| December 22, 2018 | (1) Woburn Tanners at (2) Belmont Marauders | Skip Viglirolo Rink |
| December 23, 2018 | (4) Woburn Tanners at (1) Concord-Carlisle Patriots
Jake & Joe's Holiday Tournament |
Veterans Memorial Rink |
| January 05, 2019 | (5) Arlington Spy Ponders at (2) Woburn Tanners | O'Brien Arena |
| January 07, 2019 | (2) Reading Rockets at (2) Woburn Tanners | O'Brien Arena |
| January 12, 2019 | (3) Woburn Tanners at (3) Lexington Minutemen | Hayden Ice Facility |
| January 14, 2019 | (1) Woburn Tanners at (2) Danvers Falcons | O'Brien Arena |
| January 16, 2019 | (3) Woburn Tanners at (5) Winchester Red & Black | O'Brien Arena |
| January 19, 2019 | (0) Woburn Tanners at (4) Stoneham Spartans | Stoneham Arena |
| January 26, 2019 | (2) Wakefield Warriors at (4) Woburn Tanners | O'Brien Arena |
| February 02, 2019 | (4) Woburn Tanners at (1) Belmont Marauders | Skip Viglirolo Rink |
| February 06, 2019 | (1) Woburn Tanners at (4) Arlington Spy Ponders | Ed Burns Arena |
| February 09, 2019 | (1) Woburn Tanners at (5) Reading Rockets | Burbank Ice Arena |
| February 13, 2019 | (2) Lexington Minutemen at (3) Woburn Tanners | O'Brien Arena |
| February 16, 2019 | (7) Winchester Red & Black at (3) Woburn Tanners | O'Brien Arena |
| February 20, 2019 | (3) Westford Academy Ghosts at (5) Woburn Tanners | O'Brien Arena |
| Feb. 22 (Time TBA) | (0) Milton Wildcats at (6) Woburn Tanners | O'Brien Arena |
