| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (1) Holliston Panthers at (3) Westwood Wolverines | Canton Ice House |
| December 18, 2019 | (1) Westwood Wolverines at (2) Dedham Marauders | Noble & Greenough School |
| December 21, 2019 | (1) Westwood Wolverines at (3) Hopkinton Hillers | New England Sports Center |
| December 28, 2019 | (7) Canton Bulldogs at (0) Westwood Wolverines | Canton Ice House |
| January 04, 2020 | (1) Norton Lancers at (6) Westwood Wolverines | Canton Ice House |
| January 08, 2020 | (3) Medfield Warriors at (3) Westwood Wolverines | Canton Ice House |
| January 11, 2020 | (4) Westwood Wolverines at (11) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| January 14, 2020 | (3) Ashland Clockers at (6) Westwood Wolverines | Canton Ice House |
| January 18, 2020 | (5) Westwood Wolverines at (2) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| January 20, 2020 | (4) Shrewsbury Colonials at (0) Westwood Wolverines | Canton Ice House |
| January 22, 2020 | (2) Westwood Wolverines at (3) Norwood Mustangs | Bajko Memorial Rink |
| January 25, 2020 | (1) Westwood Wolverines at (0) Holliston Panthers | Loring Arena |
| January 29, 2020 | (0) Bellingham Blackhawks at (8) Westwood Wolverines | Canton Ice House |
| February 01, 2020 | (1) Hopkinton Hillers at (2) Westwood Wolverines | Canton Ice House |
| February 05, 2020 | (0) Westwood Wolverines at (0) Medway Mustangs | Pirelli Veterans Arena |
| February 08, 2020 | (1) Westwood Wolverines at (2) Medfield Warriors | Pirelli Veterans Arena |
| February 12, 2020 | (7) Westwood Wolverines at (4) Ashland Clockers | Loring Arena |
| February 15, 2020 | (1) Norwood Mustangs at (0) Westwood Wolverines | Canton Ice House |
| February 17, 2020 | (3) Westwood Wolverines at (2) Oliver Ames Tigers | Asiaf Skating Arena |
| February 19, 2020 | (1) Bourne Canalmen at (5) Westwood Wolverines | Canton Ice House |
| February 25, 2020 | (3) Westwood Wolverines at (2) Norwood Mustangs
Boys D2 S Playoff |
Canton Ice House |
| February 29, 2020 | (3) Medway Mustangs at (2) Westwood Wolverines
Boys D2 S Playoff |
Loring Arena |
