| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (3) Nashoba Wolves at (2) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| December 15, 2018 | (3) Holliston/Ashland Panthers at (3) Medfield Warriors | Pirelli Veterans Arena |
| December 19, 2018 | (4) Westwood Wolverines at (0) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| December 22, 2018 | (2) Holliston/Ashland Panthers at (2) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 26, 2018 | (2) Hopedale / Milford Blue Raiders at (1) Holliston/Ashland Panthers
ST JOSEPH PREP CHRISTMAS CLASSIC |
Warrior Ice Arena |
| December 27, 2018 | (5) St. Joseph Prep The Phoenix at (1) Holliston/Ashland Panthers
ST JOSEPH PREP CHRISTMAS CLASSIC |
Warrior Ice Arena |
| January 02, 2019 | (4) Hopkinton Hillers at (1) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| January 05, 2019 | (2) Norwood Mustangs at (0) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| January 09, 2019 | (2) Holliston/Ashland Panthers at (4) Westboro Rangers | NorthStar Ice Sports |
| January 12, 2019 | (2) Holliston/Ashland Panthers at (2) Ashland Clockers | Loring Arena |
| January 16, 2019 | (5) Holliston/Ashland Panthers at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| January 19, 2019 | (0) Holliston/Ashland Panthers at (1) Hopkinton Hillers | Navin Arena |
| January 23, 2019 | (1) Dedham Marauders at (0) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| January 26, 2019 | (5) Medfield Warriors at (1) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| January 30, 2019 | (1) Holliston/Ashland Panthers at (5) Westwood Wolverines | Canton Ice House |
| February 02, 2019 | (0) Holliston/Ashland Panthers at (4) Medway/Bellingham/Millis Mustangs | Pirelli Veterans Arena |
| February 06, 2019 | (0) Holliston/Ashland Panthers at (7) Norwood Mustangs | Bajko Memorial Rink |
| February 09, 2019 | (5) Norton Lancers at (2) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| February 13, 2019 | (3) Ashland Clockers at (2) Holliston/Ashland Panthers | Blackstone Valley Ice Arena |
| February 20, 2019 | (5) Bedford Bucs at (3) Holliston/Ashland Panthers | Loring Arena |
