| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (4) Medway/Ashland Mustangs at (0) Framingham Flyers | Loring Arena |
| December 14, 2019 | (2) Medway/Ashland Mustangs at (5) Norwood Mustangs | Rodman Arena |
| December 18, 2019 | (4) Westwood Wolverines at (2) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| December 21, 2019 | (4) Medway/Ashland Mustangs at (1) Medfield Warriors | Boch Ice Center |
| December 29, 2019 | (2) MOA Warriors at (2) Medway/Ashland Mustangs
Medway wins 3-2 in SO |
Blackstone Valley Ice Arena |
| December 30, 2019 | (2) Natick Red Hawks at (0) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| January 04, 2020 | (1) Medway/Ashland Mustangs at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| January 06, 2020 | (0) Weymouth Wildcats at (5) Medway/Ashland Mustangs | Pirelli Veterans Arena |
| January 08, 2020 | (1) Dedham Marauders at (2) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| January 11, 2020 | (1) Medway/Ashland Mustangs at (5) King Philip Warriors | Foxboro Sports Center |
| January 18, 2020 | (2) Franklin Panthers at (3) Medway/Ashland Mustangs | New England Sports Center |
| January 22, 2020 | (3) Canton Bulldogs at (3) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| January 27, 2020 | (3) Medway/Ashland Mustangs at (3) Lexington Minutemen | Bentley Arena |
| January 29, 2020 | (4) Norwood Mustangs at (2) Medway/Ashland Mustangs | New England Sports Center |
| February 01, 2020 | (4) Medway/Ashland Mustangs at (4) Westwood Wolverines | Canton Ice House |
| February 05, 2020 | (4) Medfield Warriors at (1) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| February 08, 2020 | (0) Dover-Sherborn/Hopkinton Raiders at (3) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| February 12, 2020 | (5) Medway/Ashland Mustangs at (5) Dedham Marauders | Noble & Greenough School |
| February 17, 2020 | (3) Marshfield Rams at (6) Medway/Ashland Mustangs | Blackstone Valley Ice Arena |
| February 19, 2020 | (2) Natick Red Hawks at (3) Medway/Ashland Mustangs | New England Sports Center |
| February 26, 2020 | (2) Medway/Ashland Mustangs at (3) Arlington Spy Ponders
Girls D1 Playoff |
Ed Burns Arena |
