| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Dedham Marauders at (3) Medfield Warriors | Boch Ice Center |
| December 18, 2019 | (4) Medfield Warriors at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 21, 2019 | (4) Medway/Ashland Mustangs at (1) Medfield Warriors | Boch Ice Center |
| December 27, 2019 | (1) Medfield Warriors at (4) Canton Bulldogs
Tournament |
Canton Ice House |
| December 29, 2019 | (1) Medfield Warriors at (2) Milton Wildcats
Canton Ice House Tournament |
Canton Ice House |
| January 01, 2020 | (0) MOA Warriors at (4) Medfield Warriors | Boch Ice Center |
| January 04, 2020 | (1) Medfield Warriors at (6) Norwood Mustangs | Rodman Arena |
| January 11, 2020 | (6) Medfield Warriors at (0) Bishop Feehan Shamrocks | New England Sports Village |
| January 15, 2020 | (3) Medfield Warriors at (2) King Philip Warriors | Foxboro Sports Center |
| January 18, 2020 | (7) Medfield Warriors at (1) Winthrop Vikings | Larsen Rink |
| January 20, 2020 | (5) Westwood Wolverines at (3) Medfield Warriors | Boch Ice Center |
| January 22, 2020 | (2) Medfield Warriors at (2) Franklin Panthers | Pirelli Veterans Arena |
| January 29, 2020 | (4) Medfield Warriors at (2) Dedham Marauders | Noble & Greenough School |
| February 01, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (2) Medfield Warriors | Boch Ice Center |
| February 05, 2020 | (4) Medfield Warriors at (1) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| February 08, 2020 | (1) Norwood Mustangs at (0) Medfield Warriors | Boch Ice Center |
| February 12, 2020 | (2) Medfield Warriors at (2) Westwood Wolverines | Canton Ice House |
| February 15, 2020 | (1) Framingham Flyers at (2) Medfield Warriors | Boch Ice Center |
| February 18, 2020 | (3) Algonquin/Hudson Titans at (1) Medfield Warriors
INCLUSION CUP Tournament |
Loring Arena |
| February 20, 2020 | (3) Medfield Warriors at (1) Framingham Flyers
INCLUSION CUP Tournament |
Loring Arena |
| February 24, 2020 | (0) Bishop Stang Spartans at (5) Medfield Warriors
Girls D2 Playoff |
Boch Ice Center |
| February 29, 2020 | (0) Medfield Warriors at (3) Wellesley Raiders
Girls D2 Playoff |
Canton Ice House |
