| Date | Time | Game | |
|---|
| 09/20/2019 | 4 p.m. | KVAC: Bangor, Brewer, Brunswick, Hampden Academy, Nokomis, Skowhegan, Winslow | |
| 09/20/2019 | 4 p.m. | KVAC: Belfast, Camden Hills, Cony, Erskine Academy, Gardiner, Lawrence, Lincoln Academy, Medomak Valley, Messalonskee, Morse, Oceanside, Waterville | |
| 09/20/2019 | 4 p.m. | KVAC: Edward Little, Leavitt, Lewiston, Maranacook, Mt. Ararat, Mt. Blue, Oxford Hills | Details |
| 09/20/2019 | 4 p.m. | MVC: Carrabec, Lisbon, Madison, Mt. Abram, Oak Hill, Spruce Mountain, Winthrop | |
| 09/20/2019 | 4 p.m. | SMAA: Gorham, Portland, Scarborough, Sanford | Details |
| 09/20/2019 | 4 p.m. | SMAA: Cheverus, Marshwood, Massabesic, South Portland, Windham | |
| 09/20/2019 | 4 p.m. | SMAA: Biddeford, Deering, Falmouth, Kennebunk, Thornton Academy | |
| 09/20/2019 | 4 p.m. | WMC: Freeport, Gray-New Gloucester, Maine Coast Waldorf, Sacopee Valley, Traip Academy | Details |
| 09/20/2019 | 4 p.m. | WMC: Lake Region, North Yarmouth Academy, Poland, St. Dominic, Yarmouth, York | |
| 09/19/2019 | 4 p.m. | WMC: Cape Elizabeth, Old Orchard Beach, Waynflete, Wells | Details |
| 09/17/2019 | | KVAC | Details |
| Date | Time | Game | |
|---|
| 09/26/2019 | 4 p.m. | KVAC: Brunswick, Lawrence, Morse, Mt. Ararat | |
| 09/26/2019 | 4 p.m. | KVAC: Lincoln Academy, Maranacook, Medomak Valley, Mt. Blue, Oceanside, Richmond | |
| 09/27/2019 | 4 p.m. | KVAC: Bangor, Belfast, Camden Hills, Cony, Edward Little, Erskine Academy, Gardiner, Hampden Academy, Mt. View, Waterville, Winslow | |
| 09/27/2019 | 4 p.m. | KVAC: Leavitt, Lewiston, Mt. Ararat, Oxford Hills | |
| 09/27/2019 | 4 p.m. | WMC: Cape Elizabeth, Greely, Waynflete, York | |
| 09/27/2019 | 4 p.m. | WMC: Freeport, Gray-New Gloucester, Maine Coast Waldorf, St. Dominic, Traip Academy, Yarmouth | |
| 09/27/2019 | 4 p.m. | WMC: North Yarmouth Academy, Old Orchard Beach, Wells, | |
| 09/28/2019 | 4 p.m. | WMC: Fryeburg Academy, Lake Region, Poland, Sacopee Valley, | |
| 10/03/2019 | 4 p.m. | SMAA: Deering, Noble, Westbrook, | |
| 10/04/2019 | 4 p.m. | KVAC: Brunswick, Gardiner, Leavitt, Morse, Mt. Ararat, Mt. View, Nokomis, Oxford Hills, Skowhegan, | |
| 10/04/2019 | 4 p.m. | WMC: Freeport, Fryeburg Academy, North Yarmouth Academy, Waynflete, | |
| 10/04/2019 | 4 p.m. | WMC: Old Orchard Beach, Sacopee Valley, Traip Academy, Wells, York, | |
