| Date | Time | Game | |
|---|
| 12/11/2019 | 5 p.m. | Belfast|Erskine Academy at Mt. View | |
| 12/11/2019 | 6 p.m. | Camden Hills, Mt. Blue at Gardiner | |
| 12/11/2019 | 5 p.m. | Cheverus, Scarborough at Marshwood | |
| 12/11/2019 | 5 p.m. | Fryeburg Academy at Deering | |
| 12/11/2019 | 6 p.m. | Lincoln Academy, Lisbon/Oak Hill at Medomak Valley | |
| 12/11/2019 | 5 p.m. | Massabesic, Noble at Kennebunk | |
| 12/11/2019 | 5 p.m. | Monmouth Academy at Madison | |
| 12/11/2019 | 6 p.m. | Nokomis, Oxford Hills at Skowhegan | |
| 12/11/2019 | 6 p.m. | Sanford at Windham/Gray-New Gloucester | |
| 12/14/2019 | 9 a.m. | Camden Hills, Medomak Valley, Mt. View, Oceanside, Winslow at Mt. Ararat/Brunswick | |
| 12/14/2019 | 9 a.m. | Franklin Savings Bank Invitational at Mountain Valley | |
| 12/14/2019 | 9:30 a.m. | Tiger Invitational at Gardiner | |
| 12/18/2019 | 6 p.m. | Belfast, MCI at Cony | |
| 12/18/2019 | 5 p.m. | Bonny Eagle, Portland/South Portland at Biddeford/Thornton Academy | |
| 12/18/2019 | 6 p.m. | Camden Hills, Winslow at Lincoln Academy | |
| 12/18/2019 | 5 p.m. | Cheverus at Deering | |
| 12/18/2019 | 5 p.m. | Kennebunk, Scarborough at Sanford | |
| 12/18/2019 | 6 p.m. | Marshwood at Fryeburg Academy | |
| 12/18/2019 | 6 p.m. | Massabesic, York at Windham/Gray-New Gloucester | |
| 12/18/2019 | 6 p.m. | Medomak Valley, Skowhegan at Mt. Blue | |
| 12/18/2019 | 6 p.m. | Morse at Oxford Hills | |
| 12/18/2019 | 6 p.m. | Mt. View, Oceanside at Nokomis | |
| 12/19/2019 | 6 p.m. | Gardiner, Medomak Valley at Erskine Academy | |
| 12/21/2019 | 9 a.m. | Atlantic Invitational at Wells | |
| 12/21/2019 | 11 a.m. | Belfast, Mt. View, Oceanside at Camden Hills | |
| 12/21/2019 | 9 a.m. | Cony Duals | |
| 12/21/2019 | 9 a.m. | Portland Cup at Deering | |
| 12/23/2019 | 9 a.m. | Biddeford/Thornton Academy at Massabesic | |
| 12/23/2019 | 10 a.m. | Deering at Kennebunk | |
| 12/23/2019 | 5 p.m. | Fryeburg Academy, Wells at Noble | |
| 12/23/2019 | 9 a.m. | Marshwood at Bonny Eagle | |
| 12/23/2019 | 10:30 a.m. | Portland/South Portland at Sanford | |
| 12/23/2019 | 9 a.m. | Scarborough at Windham/Gray-New Gloucester | |
