| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Canton Bulldogs at (2) Franklin Panthers | Pirelli Veterans Arena |
| December 18, 2019 | (3) Shrewsbury Colonials at (3) Canton Bulldogs | Canton Ice House |
| December 21, 2019 | (0) Masconomet Chieftains at (3) Canton Bulldogs | Canton Ice House |
| December 28, 2019 | (7) Canton Bulldogs at (0) Westwood Wolverines | Canton Ice House |
| December 30, 2019 | (3) Duxbury Dragons at (3) Canton Bulldogs | Canton Ice House |
| January 01, 2020 | (5) Canton Bulldogs at (2) Smithfield (R.I.) | Smithfield Municipal Rink |
| January 04, 2020 | (1) Canton Bulldogs at (0) Attleboro Blue Bombardiers | New England Sports Village |
| January 08, 2020 | (2) Canton Bulldogs at (0) Mansfield Hornets | Foxboro Sports Center |
| January 11, 2020 | (2) King Philip Warriors at (5) Canton Bulldogs | Canton Ice House |
| January 15, 2020 | (0) Oliver Ames Tigers at (6) Canton Bulldogs | Canton Ice House |
| January 18, 2020 | (0) Foxboro Warriors at (2) Canton Bulldogs | Canton Ice House |
| January 20, 2020 | (5) Canton Bulldogs at (2) Newburyport Clippers | Graf Rink |
| January 25, 2020 | (3) Canton Bulldogs at (1) Franklin Panthers | Pirelli Veterans Arena |
| January 29, 2020 | (1) North Attleboro Red Rocketeers at (5) Canton Bulldogs | Canton Ice House |
| February 01, 2020 | (8) Canton Bulldogs at (0) Taunton Tigers | Aleixo Arena |
| February 03, 2020 | (3) Canton Bulldogs at (1) Barnstable Red Hawks | Hyannis Youth and Community Center |
| February 08, 2020 | (7) Canton Bulldogs at (1) Bishop Feehan Shamrocks | New England Sports Village |
| February 12, 2020 | (6) Lincoln-Sudbury Warriors at (4) Canton Bulldogs | Canton Ice House |
| February 15, 2020 | (2) Canton Bulldogs at (2) Braintree Wamps | Zapustas Arena |
| February 17, 2020 | (2) Boston Latin Wolfpack at (4) Canton Bulldogs | Canton Ice House |
| February 18, 2020 | (5) Canton Bulldogs at (2) Medfield Warriors | Pirelli Veterans Arena |
| February 26, 2020 | (0) Taunton Tigers at (4) Canton Bulldogs
Boys D2 S Playoff |
Canton Ice House |
| February 29, 2020 | (2) Medfield Warriors at (6) Canton Bulldogs
Boys D2 S Playoff |
Canton Ice House |
| March 03, 2020 | (0) Whitman-Hanson Panthers at (6) Canton Bulldogs
Boys D2 S Semifinals |
Gallo Arena |
| March 08, 2020 | (1) Bishop Feehan Shamrocks at (4) Canton Bulldogs
Boys D2 S Final |
Gallo Arena |
| March 15, 2020 | Lincoln-Sudbury Warriors at Canton Bulldogs
Boys D2 Championship |
TD Garden |
