| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (1) Holliston/Ashland Panthers at (3) Westwood Wolverines | Canton Ice House |
| December 18, 2019 | (0) Dover-Sherborn/Weston Raiders at (2) Holliston/Ashland Panthers | Loring Arena |
| December 21, 2019 | (5) Holliston/Ashland Panthers at (1) St. Joseph Prep The Phoenix | Warrior Ice Arena |
| December 23, 2019 | (2) Dover-Sherborn/Weston Raiders at (6) Holliston/Ashland Panthers
ST JOSEPH PREP HOLDIAY TOURNAMENT |
Warrior Ice Arena |
| December 30, 2019 | (0) East Boston Jets at (1) Holliston/Ashland Panthers | Loring Arena |
| January 01, 2020 | (0) Gardner/Murdock Wildcats at (7) Holliston/Ashland Panthers | Loring Arena |
| January 04, 2020 | (1) Nantucket Whalers at (4) Holliston/Ashland Panthers | Loring Arena |
| January 08, 2020 | (3) Holliston/Ashland Panthers at (2) Ashland Clockers | Loring Arena |
| January 11, 2020 | (0) Bellingham Blackhawks at (3) Holliston/Ashland Panthers | Loring Arena |
| January 13, 2020 | (1) Holliston/Ashland Panthers at (2) Norwood Mustangs | Bajko Memorial Rink |
| January 15, 2020 | (4) Hopkinton Hillers at (2) Holliston/Ashland Panthers | Loring Arena |
| January 18, 2020 | (2) Holliston/Ashland Panthers at (2) Dedham Marauders | Noble & Greenough School |
| January 22, 2020 | (2) Holliston/Ashland Panthers at (2) Medfield Warriors | New England Sports Center |
| January 25, 2020 | (1) Westwood Wolverines at (0) Holliston/Ashland Panthers | Loring Arena |
| January 29, 2020 | (4) Medway/Bellingham/Millis Mustangs at (0) Holliston/Ashland Panthers | Loring Arena |
| February 01, 2020 | (4) Norwood Mustangs at (3) Holliston/Ashland Panthers | Loring Arena |
| February 05, 2020 | (6) Holliston/Ashland Panthers at (0) Norton Lancers | Foxboro Sports Center |
| February 08, 2020 | (0) Ashland Clockers at (4) Holliston/Ashland Panthers | Loring Arena |
| February 12, 2020 | (0) Holliston/Ashland Panthers at (3) Hopkinton Hillers | New England Sports Center |
| February 14, 2020 | (7) Medfield Warriors at (2) Holliston/Ashland Panthers | Loring Arena |
| February 24, 2020 | (5) Silver Lake Lakers at (2) Holliston/Ashland Panthers
Boys D3 S Playoff |
Loring Arena |
