| Date | Time | Game | |
|---|
| 09/21/2019 | 11 a.m. | York at Marshwood | |
| 09/21/2019 | | Mt. Desert Island 3, Cony 0 | |
| 09/21/2019 | 1:30 p.m. | George Stevens at Calais | |
| 09/21/2019 | | Machias 3, Lee/Mattanawcook 0 | |
| 09/20/2019 | 5:30 p.m. | Bucksport at George Stevens | |
| 09/20/2019 | 6 p.m. | Cape Elizabeth at Deering | |
| 09/20/2019 | | Washington Academy 3, Ellsworth 0 | |
| 09/20/2019 | | Falmouth 3, Greely 0 | Details |
| 09/20/2019 | | Jonesport-Beals 3, Machias 1 | |
| 09/20/2019 | 5 p.m. | Narraguagus at Woodland | |
| 09/20/2019 | | Brewer 3, Nokomis 0 | |
| 09/20/2019 | | North Yarmouth Academy 3, Cony 2 | |
| 09/20/2019 | | Cheverus 3, Westbrook 0 | Details |
| 09/20/2019 | 5:30 p.m. | Yarmouth at York | |
| 09/19/2019 | | South Portland 3, Bonny Eagle 0 | Details |
| 09/19/2019 | 5 p.m. | Calais at Lee/Mattanawcook | |
| 09/19/2019 | | George Stevens 3, Jonesport-Beals 0 | |
| 09/19/2019 | | Gorham 3, Biddeford 0 | Details |
| 09/19/2019 | | Thornton Academy 3, Kennebunk 0 | |
| 09/19/2019 | | Marshwood 3, Massabesic 2 | |
| 09/19/2019 | | Portland 3, Brunswick/Mt. Ararat 2 | Details |
| 09/19/2019 | | Sanford/Noble 3, Westbrook 0 | Details |
| 09/19/2019 | | Scarborough 3, Windham 1 | Details |
| 09/18/2019 | | Narraguagus 3, Sumner 0 | |
| 09/18/2019 | | Bucksport 3, Brewer 2 | |
| 09/18/2019 | | Washington Academy 3, Mt. Desert Island 0 | |
| 09/18/2019 | | York 3, North Yarmouth Academy 0 | Details |
| 09/17/2019 | | Bonny Eagle 3, Biddeford 2 | Details |
| 09/17/2019 | | Windham 3, Brunswick/Mt. Ararat 1 | Details |
| 09/17/2019 | | Cape Elizabeth 3, Nokomis 0 | |
| 09/17/2019 | | Cheverus 3, Greely 1 | Details |
| 09/17/2019 | | Gardiner 3, Ellsworth 0 | |
| 09/17/2019 | | Falmouth 3, Deering 0 | |
| 09/17/2019 | | Massabesic 3, Kennebunk 2 | |
| 09/17/2019 | | York 3, Sanford/Noble 1 | |
| 09/17/2019 | 6 p.m. | Scarborough at Gorham | |
| 09/17/2019 | | South Portland 3, Marshwood 0 | |
| 09/17/2019 | | Thornton Academy 3, Portland 1 | Details |
| 09/16/2019 | | Wells 3, Lake Region 0 | |
| 09/16/2019 | | Woodland 3, Machias 0 | |
| 09/16/2019 | | Calais 3, Narraguagus 1 | |
| 09/16/2019 | | Sumner 3, Lee/Mattanawcook 1 | |
| 09/14/2019 | | Bucksport 3, Lake Region 0 | |
| 09/14/2019 | | George Stevens 3, Lake Region 0 | |
| 09/14/2019 | | Mt. Desert Island 3, Westbrook 0 | |
| 09/14/2019 | | North Yarmouth Academy 3, Bucksport 2 | |
| 09/14/2019 | | George Stevens 3, North Yarmouth Academy 0 | |
| 09/14/2019 | | Yarmouth 3, Washington Academy 0 | Details |
| 09/14/2019 | | Cape Elizabeth 3, Wells 0 | Details |
| Date | Time | Game | |
|---|
| 09/23/2019 | 5:30 p.m. | Ellsworth at George Stevens | |
| 09/23/2019 | 5 p.m. | Lee/Mattanawcook at Woodland | |
| 09/23/2019 | 5 p.m. | Washington Academy at Calais | |
| 09/24/2019 | 6 p.m. | Biddeford at Marshwood | |
| 09/24/2019 | 6 p.m. | Brewer at Gardiner | |
| 09/24/2019 | 6 p.m. | Brunswick/Mt. Ararat at Kennebunk | |
| 09/24/2019 | 5:30 p.m. | Bucksport at Lee/Mattanawcook | |
| 09/24/2019 | 6 p.m. | Cheverus at Massabesic | |
| 09/24/2019 | 6 p.m. | Cony at Westbrook | |
| 09/24/2019 | 6 p.m. | Deering at Bonny Eagle | |
| 09/24/2019 | 5:30 p.m. | Falmouth at Portland | |
| 09/24/2019 | 4 p.m. | Narraguagus at Jonesport-Beals | |
| 09/24/2019 | 6 p.m. | Nokomis at Yarmouth | |
| 09/24/2019 | 6 p.m. | Scarborough at Cape Elizabeth | |
| 09/24/2019 | 6 p.m. | South Portland at Windham | |
| 09/24/2019 | 5:30 p.m. | Sumner at George Stevens | |
| 09/24/2019 | 4:30 p.m. | Thornton Academy at Sanford/Noble | |
| 09/24/2019 | 5:30 p.m. | Wells at York | |
| 09/25/2019 | 5 p.m. | Calais at Woodland | |
| 09/25/2019 | 6 p.m. | Wells at Lake Region | |
| 09/26/2019 | 6:30 p.m. | Biddeford at Thornton Academy | |
| 09/26/2019 | 6 p.m. | Bonny Eagle at Brunswick/Mt. Ararat | |
| 09/26/2019 | 5:30 p.m. | Bucksport at Sumner | |
| 09/26/2019 | 6 p.m. | Cony at Brewer | |
| 09/26/2019 | 4 p.m. | George Stevens at Narraguagus | |
| 09/26/2019 | 6 p.m. | Kennebunk at Deering | |
| 09/26/2019 | 6:30 p.m. | Marshwood at Falmouth | |
| 09/26/2019 | 5:30 p.m. | Mt. Desert Island at Ellsworth | |
| 09/26/2019 | 6 p.m. | Portland at Scarborough | |
| 09/26/2019 | 7 p.m. | Sanford/Noble at South Portland | |
| 09/26/2019 | 6 p.m. | Windham at Gorham | |
| 09/26/2019 | 6 p.m. | York at Massabesic | |
| 09/27/2019 | 4 p.m. | Cape Elizabeth at Westbrook | |
| 09/27/2019 | 6 p.m. | Gardiner at Greely | |
| 09/27/2019 | 5:30 p.m. | Sumner at Machias | |
| 09/27/2019 | 4 p.m. | Westbrook at North Yarmouth Academy | |
| 09/27/2019 | 7 p.m. | Yarmouth at Washington Academy | |
| 09/28/2019 | 12 p.m. | Calais at Lake Region | |
| 09/28/2019 | 2:30 p.m. | Calais at North Yarmouth Academy | |
| 09/28/2019 | 12:30 p.m. | Greely at Mt. Desert Island | |
| 09/28/2019 | 2 p.m. | Lee/Mattanawcook at Jonesport-Beals | |
| 09/28/2019 | 10 a.m. | Nokomis at Westbrook | |
| 09/28/2019 | 2:30 p.m. | Woodland at Lake Region | |
| 09/28/2019 | 1 p.m. | Woodland at North Yarmouth Academy | |
| 09/28/2019 | 12:30 p.m. | Yarmouth at Brewer | |
| 09/30/2019 | 5 p.m. | Lee/Mattanawcook at Calais | |
| 09/30/2019 | 4:30 p.m. | Woodland at Narraguagus | |
| 10/01/2019 | 5:30 p.m. | Brewer at Washington Academy | |
| 10/01/2019 | 6 p.m. | Cony at Lake Region | |
| 10/01/2019 | 6 p.m. | Deering at Windham | |
| 10/01/2019 | 5:30 p.m. | Falmouth at Biddeford | |
| 10/01/2019 | 6 p.m. | Gorham at Cheverus | |
| 10/01/2019 | 4:30 p.m. | Jonesport-Beals at Narraguagus | |
| 10/01/2019 | 6 p.m. | Massabesic at Bonny Eagle | |
| 10/01/2019 | 6 p.m. | Nokomis at Greely | |
| 10/01/2019 | 6 p.m. | Sanford/Noble at Portland | |
| 10/01/2019 | 6 p.m. | Scarborough at Marshwood | |
| 10/01/2019 | 6:30 p.m. | South Portland at Thornton Academy | |
| 10/01/2019 | 5:30 p.m. | Sumner at Machias | |
| 10/01/2019 | 5:30 p.m. | Westbrook at Ellsworth | |
| 10/01/2019 | 5:30 p.m. | Yarmouth at Wells | |
| 10/02/2019 | 5:30 p.m. | Kennebunk at York | |
| 10/02/2019 | 5 p.m. | Woodland at Lee/Mattanawcook | |
| 10/03/2019 | 6 p.m. | Biddeford at Cheverus | |
| 10/03/2019 | 5:30 p.m. | Bonny Eagle at Portland | |
| 10/03/2019 | 6 p.m. | Brunswick/Mt. Ararat at Gorham | |
| 10/03/2019 | 7 p.m. | Deering at South Portland | |
| 10/03/2019 | 6 p.m. | Ellsworth at Brewer | |
| 10/03/2019 | 6 p.m. | Falmouth at Scarborough | |
| 10/03/2019 | 5:30 p.m. | George Stevens at Bucksport | |
| 10/03/2019 | 6 p.m. | Marshwood at Kennebunk | |
| 10/03/2019 | 6 p.m. | Thornton Academy at Massabesic | |
| 10/03/2019 | 4:30 p.m. | Windham at Sanford/Noble | |
| 10/03/2019 | 6 p.m. | York at Cape Elizabeth | |
| 10/04/2019 | 6 p.m. | Greely at Cony | |
| 10/04/2019 | 5:30 p.m. | Jonesport-Beals at Sumner | |
| 10/04/2019 | 5:30 p.m. | Mt. Desert Island at Nokomis | |
| 10/04/2019 | 4 p.m. | Narraguagus at Lee/Mattanawcook | |
| 10/04/2019 | 6 p.m. | Sanford/Noble at Cheverus | |
| 10/04/2019 | 5:30 p.m. | Westbrook at Gardiner | |
| 10/05/2019 | 10:30 a.m. | Brunswick/Mt. Ararat at Falmouth | |
| 10/05/2019 | 12:30 p.m. | Gardiner at Mt. Desert Island | |
| 10/05/2019 | 2:30 p.m. | North Yarmouth Academy at Nokomis | |
| 10/05/2019 | 10:30 a.m. | Portland at Windham | |
| 10/05/2019 | 6 p.m. | Scarborough at Yarmouth | |
| 10/05/2019 | 11:30 a.m. | Washington Academy at Ellsworth | |
