| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) Plymouth South Panthers at (5) Plymouth North Eagles | Gallo Arena |
| December 14, 2019 | (10) Plymouth North Eagles at (1) Martha's Vineyard Vineyarders
Jim Gormley Cup |
Gallo Arena |
| December 18, 2019 | (2) Silver Lake Lakers at (2) Plymouth North Eagles | Armstrong Arena |
| December 21, 2019 | (5) Plymouth North Eagles at (2) North Quincy Red Raiders | Quincy Youth Arena |
| December 30, 2019 | (4) Plymouth North Eagles at (0) Old Rochester/Fairhaven Bulldogs | Tabor Academy |
| January 03, 2020 | (4) Plymouth North Eagles at (1) Quincy Presidents | Quincy Youth Arena |
| January 06, 2020 | (1) Marblehead Magicians at (1) Plymouth North Eagles | Armstrong Arena |
| January 08, 2020 | (1) Duxbury Dragons at (4) Plymouth North Eagles | Armstrong Arena |
| January 11, 2020 | (4) Plymouth North Eagles at (1) Whitman-Hanson Panthers | Rockland Arena |
| January 15, 2020 | (5) Plymouth North Eagles at (1) Plymouth South Panthers | Armstrong Arena |
| January 18, 2020 | (0) Plymouth North Eagles at (3) Hanover Hawks | Hobomock Arena |
| January 22, 2020 | (1) Scituate Sailors at (2) Plymouth North Eagles | Armstrong Arena |
| January 25, 2020 | (3) Plymouth North Eagles at (5) Marshfield Rams | Hobomock Arena |
| January 29, 2020 | (0) Whitman-Hanson Panthers at (2) Plymouth North Eagles | Armstrong Arena |
| February 01, 2020 | (0) Plymouth North Eagles at (1) Duxbury Dragons | The Bog |
| February 05, 2020 | (0) Pembroke Titans at (6) Plymouth North Eagles | Armstrong Arena |
| February 08, 2020 | (1) Plymouth North Eagles at (0) Silver Lake Lakers | Hobomock Arena |
| February 12, 2020 | (2) Quincy Presidents at (4) Plymouth North Eagles | Armstrong Arena |
| February 15, 2020 | (4) Hopkinton Hillers at (2) Plymouth North Eagles
Fairleigh Dickenson Tournament |
Martha's Vineyard Arena |
| February 16, 2020 | (0) Attleboro Blue Bombardiers at (4) Plymouth North Eagles
Tournament |
Martha's Vineyard Arena |
| February 18, 2020 | (0) Old Rochester/Fairhaven Bulldogs at (6) Plymouth North Eagles | Armstrong Arena |
| February 26, 2020 | (3) Bishop Feehan Shamrocks at (2) Plymouth North Eagles
Boys Div 2S Playoffs |
Gallo Arena |
