| Date |
Game |
Results |
| 01/14/2019 | Portland/South Portland at Scarborough |
| 01/16/2019 | Kennebunk at Bonny Eagle |
| 01/16/2019 | Noble at Marshwood | Details |
| 01/16/2019 | Mt. Ararat/Brunswick at Belfast |
| 01/16/2019 | Nokomis at Belfast |
| 01/16/2019 | Mt. Ararat/Brunswick vs. Nokomis |
| 01/16/2019 | Monmouth Academy at Erskine Academy | Details |
| 01/16/2019 | Oceanside at Erskine Academy | Details |
| 01/16/2019 | Monmouth Academy vs. Oceanside |
| 01/16/2019 | Dirigo at Fryeburg Academy |
| 01/16/2019 | Lisbon/Oak Hill at Fryeburg Academy |
| 01/16/2019 | Dirigo vs. Lisbon/Oak Hill |
| 01/16/2019 | Mt. Blue/Spruce Mountain at Gardiner |
| 01/16/2019 | Winslow at Gardiner |
| 01/16/2019 | Mt. Blue/Spruce Mountain vs. Winslow |
| 01/16/2019 | Lincoln Academy at MCI |
| 01/16/2019 | Skowhegan at MCI |
| 01/16/2019 | Lincoln Academy vs. Skowhegan |
| 01/16/2019 | Camden Hills at Medomak Valley |
| 01/16/2019 | Cony at Medomak Valley |
| 01/16/2019 | Camden Hills vs. Cony |
| 01/16/2019 | Mt. View at Morse |
| 01/16/2019 | Oxford Hills at Morse |
| 01/16/2019 | Mt. View vs. Oxford Hills |
| 01/16/2019 | Scarborough at Sanford |
| 01/16/2019 | York/Traip Academy at Sanford |
| 01/16/2019 | Scarborough vs. York/Traip Academy |
| 01/16/2019 | Wells at Biddeford |
| 01/16/2019 | Westbrook/Gorham at Windham/Gray-New Gloucester |
| 01/19/2019 | Cheverus Invitational | Details |
| 01/21/2019 | Dirigo at Madison |
| 01/21/2019 | Lincoln Academy at Madison |
| 01/21/2019 | Medomak Valley at Madison |
| 01/21/2019 | Mt. View at Madison |
| 01/21/2019 | Wells at Madison |
| 01/21/2019 | Dirigo vs. Lincoln Academy |
| 01/21/2019 | Dirigo vs. Medomak Valley |
| 01/21/2019 | Dirigo vs. Mt. View |
| 01/21/2019 | Dirigo vs. Wells |
| 01/21/2019 | Lincoln Academy vs. Medomak Valley |
| 01/21/2019 | Lincoln Academy vs. Mt. View |
| 01/21/2019 | Lincoln Academy vs. Wells |
| 01/21/2019 | Medomak Valley vs. Mt. View |
| 01/21/2019 | Medomak Valley vs. Wells |
| 01/21/2019 | Mt. View vs. Wells |
| 01/21/2019 | Westbrook/Gorham at Kennebunk |
| Date |
Time |
Game |
|
| 01/23/2019 | 6 p.m. | Biddeford vs. Sanford |
| 01/23/2019 | 6 p.m. | Biddeford Windham/Gray-New Gloucester |
| 01/23/2019 | 5 p.m. | Deering at Scarborough |
| 01/23/2019 | 5 p.m. | Deering vs. Massabesic |
| 01/23/2019 | 5 p.m. | Massabesic at Scarborough |
| 01/23/2019 | 6 p.m. | Medomak Valley at Monmouth Academy |
| 01/23/2019 | 6 p.m. | Medomak Valley vs. Winslow |
| 01/23/2019 | 5 p.m. | Mountain Valley at Lisbon/Oak Hill |
| 01/23/2019 | 5 p.m. | Mountain Valley vs. Richmond |
| 01/23/2019 | 6 p.m. | Mt. Ararat/Brunswick at Morse |
| 01/23/2019 | 5 p.m. | Portland/South Portland at Cheverus |
| 01/23/2019 | 5 p.m. | Richmond at Lisbon/Oak Hill |
| 01/23/2019 | 6 p.m. | Sanford at Windham/Gray-New Gloucester |
| 01/23/2019 | 6 p.m. | Winslow at Monmouth Academy |
| 01/25/2019 | 6 p.m. | KVAC Meet at Mt. Ararat |
| 01/26/2019 | 9 a.m. | Biddeford at Deering |
| 01/26/2019 | 9 a.m. | Biddeford vs. Bonny Eagle |
| 01/26/2019 | 9 a.m. | Biddeford vs. Sanford |
| 01/26/2019 | 9 a.m. | Biddeford vs. Windham/Gray-New Gloucester |
| 01/26/2019 | 9 a.m. | Bonny Eagle at Deering |
| 01/26/2019 | 9 a.m. | Bonny Eagle vs. Sanford |
| 01/26/2019 | 9 a.m. | Bonny Eagle vs. Windham/Gray-New Gloucester |
| 01/26/2019 | 9 a.m. | Cheverus at Scarborough |
| 01/26/2019 | 9 a.m. | Cheverus vs. Kennebunk |
| 01/26/2019 | 9 a.m. | Cheverus vs. Marshwood |
| 01/26/2019 | 9 a.m. | Kennebunk at Scarborough |
| 01/26/2019 | 9 a.m. | Kennebunk vs. Marshwood |
| 01/26/2019 | 9 a.m. | Lincoln Academy at Belfast |
| 01/26/2019 | 9 a.m. | Lincoln Academy vs. Ellsworth |
| 01/26/2019 | 9 a.m. | Lincoln Academy vs. Penobscot Valley |
| 01/26/2019 | 9 a.m. | Marshwood at Scarborough |
| 01/26/2019 | 9 a.m. | Massabesic at Portland/South Portland |
| 01/26/2019 | 9 a.m. | Massabesic vs. Noble |
| 01/26/2019 | 9 a.m. | Massabesic vs. Westbrook/Gorham |
| 01/26/2019 | 9 a.m. | Morse at Belfast |
| 01/26/2019 | 9 a.m. | Morse vs. Ellsworth |
| 01/26/2019 | 9 a.m. | Morse vs. Lincoln Academy |
| 01/26/2019 | 9 a.m. | Morse vs. Penobscot Valley |
| 01/26/2019 | 9 a.m. | Noble at Portland/South Portland |
| 01/26/2019 | 9 a.m. | Noble vs. Westbrook/Gorham |
| 01/26/2019 | 9 a.m. | Sanford at Deering |
| 01/26/2019 | 9 a.m. | Sanford vs. Windham/Gray-New Gloucester |
| 01/26/2019 | 9 a.m. | Westbrook/Gorham at Portland/South Portland |
| 01/26/2019 | 9 a.m. | Windham/Gray-New Gloucester at Deering |
| 01/30/2019 | 6 p.m. | Bonny Eagle at Noble |
| 01/30/2019 | | Bonny Eagle vs. Scarborough |
| 01/30/2019 | 6 p.m. | Deering at Massabesic |
| 01/30/2019 | 6 p.m. | Kennebunk at Sanford |
| 01/30/2019 | 6 p.m. | Kennebunk vs. Portland/South Portland |
| 01/30/2019 | 5 p.m. | Marshwood at Biddeford |
| 01/30/2019 | 5 p.m. | Marshwood vs. Westbrook/Gorham |
| 01/30/2019 | 6 p.m. | Portland/South Portland at Sanford |
| 01/30/2019 | 6 p.m. | Scarborough at Noble |
| 01/30/2019 | 5 p.m. | Westbrook/Gorham at Biddeford |
| 01/30/2019 | 5 p.m. | Windham/Gray-New Gloucester at Cheverus |
| 02/02/2019 | 10 a.m. | Biddeford at Kennebunk |
| 02/02/2019 | 10 a.m. | Biddeford vs. Massabesic |
| 02/02/2019 | 9 a.m. | Deering at Westbrook/Gorham |
| 02/02/2019 | 9 a.m. | Deering vs. Scarborough |
| 02/02/2019 | 9 a.m. | Marshwood at Bonny Eagle |
| 02/02/2019 | 9 a.m. | Marshwood vs. Portland/South Portland |
| 02/02/2019 | 9 a.m. | Marshwood vs. Windham/Gray-New Gloucester |
| 02/02/2019 | 10 a.m. | Massabesic at Kennebunk |
| 02/02/2019 | 10 a.m. | Noble at Cheverus |
| 02/02/2019 | 10 a.m. | Noble vs. Sanford |
| 02/02/2019 | 9 a.m. | Portland/South Portland at Bonny Eagle |
| 02/02/2019 | 9 a.m. | Portland/South Portland vs. Windham/Gray-New Gloucester |
| 02/02/2019 | 10 a.m. | Sanford at Cheverus |
| 02/02/2019 | 9 a.m. | Scarborough at Westbrook/Gorham |
| 02/02/2019 | 9 a.m. | Windham/Gray-New Gloucester at Bonny Eagle |
