| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (3) Hopkinton Hillers at (2) Medfield Warriors | Pirelli Veterans Arena |
| December 18, 2019 | (1) Norton Lancers at (3) Medfield Warriors | Pirelli Veterans Arena |
| December 21, 2019 | (3) Ashland Clockers at (3) Medfield Warriors | Pirelli Veterans Arena |
| December 22, 2019 | (3) Medfield Warriors at (2) Burrillville (R.I.) | Levy Ice Rink |
| December 30, 2019 | (1) Lynnfield Pioneers at (4) Medfield Warriors | Pirelli Veterans Arena |
| January 04, 2020 | (4) Dedham Marauders at (1) Medfield Warriors | Pirelli Veterans Arena |
| January 08, 2020 | (3) Medfield Warriors at (3) Westwood Wolverines | Canton Ice House |
| January 11, 2020 | (2) Medway Mustangs at (3) Medfield Warriors | Pirelli Veterans Arena |
| January 16, 2020 | (6) Norwood Mustangs at (5) Medfield Warriors | Pirelli Veterans Arena |
| January 18, 2020 | (5) Medfield Warriors at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| January 20, 2020 | (1) Bishop Feehan Shamrocks at (4) Medfield Warriors | Pirelli Veterans Arena |
| January 22, 2020 | (2) Holliston Panthers at (2) Medfield Warriors | New England Sports Center |
| January 25, 2020 | (3) Medfield Warriors at (6) Hopkinton Hillers | New England Sports Center |
| February 01, 2020 | (2) Medfield Warriors at (2) Ashland Clockers | Loring Arena |
| February 05, 2020 | (8) Medfield Warriors at (0) Dover-Sherborn/Weston Raiders | Chase Arena |
| February 08, 2020 | (1) Westwood Wolverines at (2) Medfield Warriors | Pirelli Veterans Arena |
| February 12, 2020 | (5) Medfield Warriors at (0) Norwood Mustangs | Bajko Memorial Rink |
| February 14, 2020 | (7) Medfield Warriors at (2) Holliston Panthers | Loring Arena |
| February 18, 2020 | (5) Canton Bulldogs at (2) Medfield Warriors | Pirelli Veterans Arena |
| February 19, 2020 | (5) Medfield Warriors at (2) Boston Latin Wolfpack | Murphy Memorial Rink |
| February 25, 2020 | (3) Medfield Warriors at (0) Dighton-Rehoboth/Seekonk Falcons
Boys D2 S Playoff |
Gallo Arena |
| February 29, 2020 | (2) Medfield Warriors at (6) Canton Bulldogs
Boys D2 S Playoff |
Canton Ice House |
