| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (2) Oliver Ames Tigers at (3) Medway Mustangs | Pirelli Veterans Arena |
| December 19, 2019 | (2) Norwood Mustangs at (2) Medway Mustangs | Pirelli Veterans Arena |
| December 26, 2019 | (4) Lewiston (Maine) at (0) Medway Mustangs
Norway Savings Bank Arena Tournament |
Norway Savings Bank Arena |
| December 27, 2019 | (0) St. Thomas Aquinas (N.H.) at (3) Medway Mustangs
Norway Savings Bank Arena Tournament |
Norway Savings Bank Arena |
| December 28, 2019 | (0) Edward Little (Maine) at (2) Medway Mustangs | Norway Savings Bank Arena |
| January 01, 2020 | (6) Medway Mustangs at (4) King Philip Warriors | Foxboro Sports Center |
| January 04, 2020 | (3) Medway Mustangs at (6) Hopkinton Hillers | New England Sports Center |
| January 08, 2020 | (1) Bellingham Blackhawks at (4) Medway Mustangs | Pirelli Veterans Arena |
| January 11, 2020 | (2) Medway Mustangs at (3) Medfield Warriors | Pirelli Veterans Arena |
| January 15, 2020 | (2) Medway Mustangs at (2) Bishop Feehan Shamrocks | New England Sports Village |
| January 18, 2020 | (4) Ashland Clockers at (4) Medway Mustangs | Pirelli Veterans Arena |
| January 22, 2020 | (2) Dedham Marauders at (3) Medway Mustangs | Pirelli Veterans Arena |
| January 25, 2020 | (4) Hudson Hawks at (4) Medway Mustangs | Pirelli Veterans Arena |
| January 29, 2020 | (4) Medway Mustangs at (0) Holliston Panthers | Loring Arena |
| February 01, 2020 | (0) Dover-Sherborn/Weston Raiders at (5) Medway Mustangs | Pirelli Veterans Arena |
| February 05, 2020 | (0) Westwood Wolverines at (0) Medway Mustangs | Pirelli Veterans Arena |
| February 08, 2020 | (6) Medway Mustangs at (1) Bellingham Blackhawks | Pirelli Veterans Arena |
| February 12, 2020 | (2) Norton Lancers at (8) Medway Mustangs | Pirelli Veterans Arena |
| February 15, 2020 | (1) Medway Mustangs at (0) Dedham Marauders | Noble & Greenough School |
| February 19, 2020 | (7) Medway Mustangs at (1) Dover-Sherborn/Weston Raiders | MacDowell Ice Arena |
| February 25, 2020 | (0) Apponequet/Old Colony Lakers at (6) Medway Mustangs
Boys D2 S Playoff |
Canton Ice House |
| February 29, 2020 | (3) Medway Mustangs at (2) Westwood Wolverines
Boys D2 S Playoff |
Loring Arena |
| March 03, 2020 | (1) Medway Mustangs at (2) Bishop Feehan Shamrocks
Boys D2 S Semifinals |
Gallo Arena |
