| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) Plymouth South Panthers at (5) Plymouth North Eagles | Gallo Arena |
| December 14, 2019 | (3) Plymouth South Panthers at (1) Sandwich Blue Knights
Jim Gormley Cup |
Gallo Arena |
| December 18, 2019 | (3) Scituate Sailors at (4) Plymouth South Panthers | Armstrong Arena |
| December 21, 2019 | (5) Plymouth South Panthers at (5) Pembroke Titans | Hobomock Arena |
| December 23, 2019 | (2) Plymouth South Panthers at (4) Stoneham Spartans | Stoneham Arena |
| December 26, 2019 | (0) Plymouth South Panthers at (8) Groton-Dunstable Crusaders
Stoneham Holiday Classic |
Stoneham Arena |
| January 04, 2020 | (1) Plymouth South Panthers at (6) North Quincy Red Raiders | Quincy Youth Arena |
| January 08, 2020 | (7) Hanover Hawks at (2) Plymouth South Panthers | Armstrong Arena |
| January 11, 2020 | (2) Plymouth South Panthers at (6) Quincy Presidents | Quincy Youth Arena |
| January 15, 2020 | (5) Plymouth North Eagles at (1) Plymouth South Panthers | Armstrong Arena |
| January 18, 2020 | (0) Plymouth South Panthers at (6) Silver Lake Lakers | Hobomock Arena |
| January 20, 2020 | (4) Plymouth South Panthers at (3) St. John Paul II Lions | Hyannis Youth and Community Center |
| January 22, 2020 | (6) Whitman-Hanson Panthers at (0) Plymouth South Panthers | Armstrong Arena |
| January 25, 2020 | (1) Plymouth South Panthers at (9) Scituate Sailors | Hobomock Arena |
| January 29, 2020 | (4) Duxbury Dragons at (2) Plymouth South Panthers | Armstrong Arena |
| February 01, 2020 | (0) Plymouth South Panthers at (7) Hanover Hawks | Hobomock Arena |
| February 05, 2020 | (7) North Quincy Red Raiders at (2) Plymouth South Panthers | Armstrong Arena |
| February 08, 2020 | (2) Plymouth South Panthers at (5) St. John Paul II Lions | Hyannis Youth and Community Center |
| February 12, 2020 | (3) Pembroke Titans at (5) Plymouth South Panthers | Armstrong Arena |
| February 15, 2020 | (1) Plymouth South Panthers at (7) Marshfield Rams | Hobomock Arena |
| February 19, 2020 | (2) Plymouth South Panthers at (7) Brookline Warriors | Walter Brown Arena |
