| Date | Time | Game | |
|---|
| 05/13/2019 | 4 p.m. | John Bapst 4, Foxcroft Academy 1 | |
| 05/13/2019 | 4 p.m. | Camden Hills 4, Mt. Ararat 1 | Details |
| 05/13/2019 | 4 p.m. | Morse 4, Belfast 1 | Details |
| 05/13/2019 | 4 p.m. | Maranacook 5, MCI 0 | Details |
| 05/13/2019 | 4 p.m. | Medomak Valley 3, Winslow 2 | |
| 05/13/2019 | 3:30 p.m. | Houlton at Presque Isle | |
| 05/13/2019 | 4 p.m. | Thornton Academy at Marshwood | |
| 05/13/2019 | 4 p.m. | Cape Elizabeth 5, Lake Region 0 | |
| 05/13/2019 | 3:45 p.m. | Scarborough 5, Biddeford 0 | Details |
| 05/13/2019 | 3:30 p.m. | Deering 3, Bonny Eagle 2 | Details |
| 05/13/2019 | 4 p.m. | Gardiner 4, Brewer 1 | |
| 05/13/2019 | 4 p.m. | Mountain Valley 4, Madison 1 | Details |
| 05/13/2019 | 4 p.m. | Skowhegan 5, Oxford Hills 0 | |
| 05/13/2019 | 4 p.m. | Orono 5, Dexter 0 | |
| 05/13/2019 | 4 p.m. | South Portland 5, Sanford 0 | Details |
| 05/13/2019 | 4 p.m. | Hall-Dale 5, Dirigo 0 | Details |
| 05/13/2019 | 4 p.m. | George Stevens 5, Piscataquis 0 | |
| 05/13/2019 | 4 p.m. | Waterville 4, Oceanside 1 | |
| 05/13/2019 | 4 p.m. | Spruce Mountain 5, Wiscasset 0 | |
| 05/13/2019 | 4 p.m. | Deer Isle-Stonington 4, Sumner 1 | |
| 05/13/2019 | 3:30 p.m. | Freeport 3, St. Dominic 2 | Details |
| 05/13/2019 | 4 p.m. | Bangor 3, Edward Little 2 | Details |
| 05/13/2019 | 4 p.m. | Washington Academy 3, Ellsworth 2 | |
| 05/13/2019 | 4 p.m. | Lewiston 5, Hampden Academy 0 | Details |
| 05/13/2019 | 4 p.m. | Greely 4, Waynflete 1 | Details |
| 05/13/2019 | 3:30 p.m. | Falmouth 4, Gorham 1 | Details |
| 05/13/2019 | 4 p.m. | Brunswick 4, Messalonskee 1 | Details |
| 05/13/2019 | 4 p.m. | Cheverus 3, Kennebunk/Wells 2 | Details |
| 05/13/2019 | 4 p.m. | Lincoln Academy 4, Erskine Academy 1 | |
| 05/13/2019 | 4 p.m. | Windham 5, Westbrook 0 | Details |
| 05/13/2019 | 3:30 p.m. | Mt. Blue 3, Cony 2 | Details |
| 05/13/2019 | 4 p.m. | Winthrop 5, Oak Hill 0 | Details |
| 05/13/2019 | 4 p.m. | Mt. Desert Island 5, Old Town 0 | |
| 05/13/2019 | 3:45 p.m. | Portland 5, Massabesic 0 | Details |
| 05/13/2019 | 4 p.m. | Foxcroft Academy 4, John Bapst 1 | |
| 05/13/2019 | 4 p.m. | Carrabec 5, Lisbon 0 | |
| 05/14/2019 | 3:30 p.m. | Cape Elizabeth 5, Freeport 0 | Details |
| 05/14/2019 | 4 p.m. | Old Town at Washington Academy | |
| 05/14/2019 | 4 p.m. | Skowhegan 3, Edward Little 2 | Details |
| 05/14/2019 | 3:30 p.m. | Gorham 5, Bonny Eagle 0 | Details |
| 05/14/2019 | 4 p.m. | Madison 3, Wiscasset 2 | |
| 05/14/2019 | 4:30 p.m. | Portland at Scarborough | |
| 05/14/2019 | 4 p.m. | Caribou 5, Madawaska 0 | |
| 05/14/2019 | 4 p.m. | Waynflete 4, North Yarmouth Academy 1 | Details |
| 05/14/2019 | 3 p.m. | Presque Isle 3, Fort Kent 1 | |
| 05/14/2019 | | Maranacook 4, Medomak Valley 1 | Details |
| 05/15/2019 | 3:30 p.m. | Skowhegan 5, Cony 0 | |
| 05/15/2019 | 4 p.m. | Gardiner 5, Belfast 0 | |
| 05/15/2019 | 4 p.m. | Winslow 3, MCI 2 | |
| 05/15/2019 | 4 p.m. | Waterville 4, Morse 1 | Details |
| 05/15/2019 | 4 p.m. | Erskine Academy 3, Maranacook 2 | Details |
| 05/15/2019 | 4 p.m. | Thornton Academy 5, Sanford 0 | Details |
| 05/15/2019 | 4 p.m. | Freeport 5, Lake Region 0 | Details |
| 05/15/2019 | 3:30 p.m. | Westbrook 4, Bonny Eagle 1 | Details |
| 05/15/2019 | 3:30 p.m. | Calais at Washington Academy | |
| 05/15/2019 | 4:15 p.m. | Cheverus 5, Deering 0 | Details |
| 05/15/2019 | 4 p.m. | Spruce Mountain 3, Mountain Valley 2 | |
| 05/15/2019 | 4 p.m. | Messalonskee 5, Oxford Hills 0 | |
| 05/15/2019 | 3:45 p.m. | South Portland 4, Biddeford 1 | Details |
| 05/15/2019 | 4 p.m. | Foxcroft Academy 4, Dexter 1 | |
| 05/15/2019 | 3:30 p.m. | Mt. Blue 5, Camden Hills 0 | Details |
| 05/15/2019 | 4 p.m. | Medomak Valley 3, Oceanside 2 | |
| 05/15/2019 | 4:30 p.m. | Marshwood 4, Windham 1 | Details |
| 05/15/2019 | 4 p.m. | Orono 5, Deer Isle-Stonington 0 | |
| 05/15/2019 | 4 p.m. | George Stevens 3, Mt. Desert Island 0 | |
| 05/15/2019 | 4 p.m. | Hall-Dale 5, Lisbon 0 | |
| 05/15/2019 | 4 p.m. | Sumner at Piscataquis | |
| 05/15/2019 | 4 p.m. | Houlton at Schenck/Stearns | |
| 05/15/2019 | 3:30 p.m. | Brunswick 5, Mt. Ararat 0 | Details |
| 05/15/2019 | 4 p.m. | Hermon 3, John Bapst 2 | |
| 05/15/2019 | 3:30 p.m. | Bangor 4, Hampden Academy 1 | |
| 05/15/2019 | 3:30 p.m. | Dirigo 3, Madison 1 | |
| 05/15/2019 | 3 p.m. | Van Buren 4, Shead 1 | |
| 05/15/2019 | 3:30 p.m. | Gorham 5, Massabesic 0 | |
| 05/15/2019 | 3:30 p.m. | Brewer at Lincoln Academy | |
| 05/15/2019 | 4 p.m. | Falmouth 4, Kennebunk/Wells 1 | Details |
| 05/15/2019 | 4 p.m. | Winthrop 5, Wiscasset 0 | |
| 05/15/2019 | 4:30 p.m. | Van Buren 4, Shead 1 | |
| 05/15/2019 | 4 p.m. | Greely 4, North Yarmouth Academy 1 | Details |
| 05/15/2019 | 6 p.m. | Lewiston 5, Edward Little 0 | Details |
| 05/16/2019 | 3:30 p.m. | Brewer 5, Morse 0 | Details |
| 05/16/2019 | 4 p.m. | Lewiston 4, Bangor 1 | Details |
| 05/16/2019 | 4:30 p.m. | Windham 5, Sanford 0 | Details |
| 05/16/2019 | 4 p.m. | Piscataquis at Deer Isle-Stonington | |
| 05/16/2019 | 4 p.m. | Gorham 3, Portland 2 | Details |
| 05/16/2019 | 4 p.m. | Falmouth 5, Thornton Academy 0 | |
| 05/16/2019 | 3:30 p.m. | South Portland 5, Bonny Eagle 0 | Details |
| 05/16/2019 | 4 p.m. | Carrabec 4, Mountain Valley 1 | Details |
| 05/16/2019 | 3:30 p.m. | Fort Kent at Presque Isle | |
| 05/16/2019 | 3 p.m. | Shead at Woodland | |
| 05/16/2019 | 3:30 p.m. | Mattanawcook Academy 5, Penobscot Valley 0 | |
| 05/16/2019 | 4:30 p.m. | Shead at Woodland | |
| 05/16/2019 | 4 p.m. | Edward Little 5, Belfast 0 | Details |
| 05/16/2019 | 4 p.m. | Caribou 5, Houlton 0 | |
| 05/16/2019 | 4 p.m. | Cape Elizabeth 5, North Yarmouth Academy 0 | Details |
| 05/16/2019 | 4 p.m. | Hermon 3, Mt. Desert Island 2 | |
| 05/16/2019 | 4 p.m. | Ellsworth 5, Old Town 0 | |
| 05/17/2019 | 4 p.m. | Dexter at Sumner | |
| 05/17/2019 | 4 p.m. | Waynflete 3, St. Dominic 2 | Details |
| 05/17/2019 | 3:30 p.m. | Erskine Academy at Cony | |
| 05/17/2019 | 4 p.m. | Oxford Hills at MCI | |
| 05/17/2019 | 4 p.m. | Skowhegan 4, Winslow 1 | |
| 05/17/2019 | 4 p.m. | Lewiston 4, Maranacook 1 | Details |
| 05/17/2019 | 4 p.m. | Portland at Thornton Academy | |
| 05/17/2019 | 4 p.m. | York at Lake Region | |
| 05/17/2019 | 4:30 p.m. | Scarborough 3, Cheverus 2 | Details |
| 05/17/2019 | 4 p.m. | Falmouth 5, Deering 0 | Details |
| 05/17/2019 | 4:30 p.m. | Gardiner 4, Mt. Blue 1 | Details |
| 05/17/2019 | 4 p.m. | Sumner at Dexter | |
| 05/17/2019 | 4 p.m. | Lincoln Academy 5, Camden Hills 0 | |
| 05/17/2019 | 4 p.m. | Marshwood 54, Massabesic 1 | Details |
| 05/17/2019 | 3:30 p.m. | Houlton 3, Van Buren 2 | |
| 05/17/2019 | 4 p.m. | Orono 5, Schenck/Stearns 0 | |
| 05/17/2019 | 4 p.m. | Hampden Academy at Oceanside | |
| 05/17/2019 | 3:30 p.m. | Cape Elizabeth 5, Yarmouth 0 | Details |
| 05/17/2019 | 3:30 p.m. | Fort Kent 5, Madawaska 0 | |
| 05/17/2019 | 3:30 p.m. | Dirigo at Wiscasset | |
| 05/17/2019 | 4 p.m. | Sanford at Westbrook | |
| 05/17/2019 | 5 p.m. | Fort Kent 5, Madawaska 0 | |
| 05/17/2019 | 3:30 p.m. | Bonny Eagle 4, Biddeford 1 | |
| 05/17/2019 | 4 p.m. | Kennebunk/Wells 5, Windham 0 | Details |
| 05/17/2019 | 4 p.m. | Messalonskee 3, Waterville 2 | |
| 05/17/2019 | 4 p.m. | Washington Academy at John Bapst | |
| 05/17/2019 | 4 p.m. | Boothbay at Lisbon | |
| 05/17/2019 | 4 p.m. | Carrabec 5, Oak Hill 0 | Details |
| 05/18/2019 | noon | Sumner at Calais | |
| 05/18/2019 | 12 p.m. | Calais at Sumner | |
| 05/18/2019 | 4 p.m. | MCI at Waterville | |
| 05/18/2019 | 4 p.m. | Brunswick 3, Bangor 2 | Details |
| 05/18/2019 | 9 a.m. | Mt. Ararat at Medomak Valley | |
| 05/18/2019 | 12 p.m. | Schenck/Stearns at Deer Isle-Stonington | |
| 05/18/2019 | 12 p.m. | Ellsworth at Presque Isle | |
| 05/18/2019 | 12 p.m. | Van Buren at Woodland | |
| 05/18/2019 | 1:30 p.m. | Woodland at Van Buren | |
| 05/18/2019 | 1 p.m. | Old Town at Caribou | |
| 05/18/2019 | | SMAA Doubles Tournament | Details |
| 05/20/2019 | 4 p.m. | Waynflete at Yarmouth | |
| 05/20/2019 | 4 p.m. | Spruce Mountain at Carrabec | |
| 05/20/2019 | 4 p.m. | MCI at Bangor | |
| 05/20/2019 | 4 p.m. | Winslow at Messalonskee | |
| 05/20/2019 | 4 p.m. | Thornton Academy at Bonny Eagle | |
| 05/20/2019 | 4 p.m. | Cape Elizabeth at York | |
| 05/20/2019 | 4:30 p.m. | Kennebunk/Wells at Scarborough | |
| 05/20/2019 | 4 p.m. | Maranacook at Mt. Blue | |
| 05/20/2019 | 3:45 p.m. | Deering at Biddeford | |
| 05/20/2019 | 4 p.m. | Penobscot Valley at Dexter | |
| 05/20/2019 | 4 p.m. | Oak Hill at Mountain Valley | |
| 05/20/2019 | 4 p.m. | Medomak Valley at Oxford Hills | |
| 05/20/2019 | 3:30 p.m. | Brewer at Hampden Academy | |
| 05/20/2019 | 3:30 p.m. | South Portland at Portland | |
| 05/20/2019 | 3:45 p.m. | Marshwood at Sanford | |
| 05/20/2019 | 4 p.m. | Belfast at Camden Hills | |
| 05/20/2019 | 3 p.m. | Fort Kent at Houlton | |
| 05/20/2019 | 4 p.m. | Oceanside at Edward Little | |
| 05/20/2019 | 4 p.m. | Madison at Hall-Dale | |
| 05/20/2019 | 4 p.m. | Morse at Mt. Ararat | |
| 05/20/2019 | 5 p.m. | Houlton at Fort Kent | |
| 05/20/2019 | 4 p.m. | Deer Isle-Stonington at Sumner | |
| 05/20/2019 | 3:30 p.m. | Gardiner at Cony | |
| 05/20/2019 | 4 p.m. | Lisbon at Dirigo | |
| 05/20/2019 | 4 p.m. | Old Town at Ellsworth | |
| 05/20/2019 | 4 p.m. | North Yarmouth Academy at Freeport | |
| 05/20/2019 | 4 p.m. | George Stevens at Mattanawcook Academy | |
| 05/20/2019 | 4 p.m. | Yarmouth at Waynflete | |
| 05/20/2019 | 4 p.m. | Lincoln Academy at Lewiston | |
| 05/20/2019 | 4 p.m. | Waterville at Skowhegan | |
| 05/20/2019 | 4 p.m. | Gorham at Windham | |
| 05/20/2019 | 3:30 p.m. | Westbrook at Massabesic | |
| 05/20/2019 | 4 p.m. | Erskine Academy at Brunswick | |
| 05/20/2019 | 4 p.m. | Cheverus at Falmouth | |
| Date | Time | Game | |
|---|
| 05/20/2019 | 4 p.m. | Belfast at Camden Hills | |
| 05/20/2019 | 3:30 p.m. | Brewer at Hampden Academy | |
| 05/20/2019 | 4 p.m. | Cape Elizabeth at York | |
| 05/20/2019 | 4 p.m. | Cheverus at Falmouth | |
| 05/20/2019 | 4 p.m. | Deer Isle-Stonington at Sumner | |
| 05/20/2019 | 3:45 p.m. | Deering at Biddeford | |
| 05/20/2019 | 4 p.m. | Erskine Academy at Brunswick | |
| 05/20/2019 | 3 p.m. | Fort Kent at Houlton | |
| 05/20/2019 | 3:30 p.m. | Gardiner at Cony | |
| 05/20/2019 | 4 p.m. | George Stevens at Mattanawcook Academy | |
| 05/20/2019 | 4 p.m. | Gorham at Windham | |
| 05/20/2019 | 5 p.m. | Houlton at Fort Kent | |
| 05/20/2019 | 4:30 p.m. | Kennebunk/Wells at Scarborough | |
| 05/20/2019 | 4 p.m. | Lincoln Academy at Lewiston | |
| 05/20/2019 | 4 p.m. | Lisbon at Dirigo | |
| 05/20/2019 | 4 p.m. | Madison at Hall-Dale | |
| 05/20/2019 | 4 p.m. | Maranacook at Mt. Blue | |
| 05/20/2019 | 3:45 p.m. | Marshwood at Sanford | |
| 05/20/2019 | 4 p.m. | MCI at Bangor | |
| 05/20/2019 | 4 p.m. | Medomak Valley at Oxford Hills | |
| 05/20/2019 | 4 p.m. | Morse at Mt. Ararat | |
| 05/20/2019 | 4 p.m. | North Yarmouth Academy at Freeport | |
| 05/20/2019 | 4 p.m. | Oak Hill at Mountain Valley | |
| 05/20/2019 | 4 p.m. | Oceanside at Edward Little | |
| 05/20/2019 | 4 p.m. | Old Town at Ellsworth | |
| 05/20/2019 | 4 p.m. | Penobscot Valley at Dexter | |
| 05/20/2019 | 3:30 p.m. | South Portland at Portland | |
| 05/20/2019 | 4 p.m. | Spruce Mountain at Carrabec | |
| 05/20/2019 | 4 p.m. | Thornton Academy at Bonny Eagle | |
| 05/20/2019 | 4 p.m. | Waterville at Skowhegan | |
| 05/20/2019 | 4 p.m. | Waynflete at Yarmouth | |
| 05/20/2019 | 3:30 p.m. | Westbrook at Massabesic | |
| 05/20/2019 | 4 p.m. | Winslow at Messalonskee | |
| 05/20/2019 | 4 p.m. | Yarmouth at Waynflete | |
| 05/21/2019 | 3:30 p.m. | Edward Little at Cony | |
| 05/21/2019 | 4 p.m. | John Bapst at Hermon | |
| 05/21/2019 | 4 p.m. | Kennebunk/Wells at Thornton Academy | |
| 05/21/2019 | 4 p.m. | MCI at Belfast | |
| 05/21/2019 | 4 p.m. | Messalonskee at Bangor | |
| 05/21/2019 | 4 p.m. | Mt. Desert Island at Washington Academy | |
| 05/21/2019 | 3 p.m. | Penobscot Valley at Schenck/Stearns | |
| 05/21/2019 | 3:45 p.m. | South Portland at Massabesic | |
| 05/21/2019 | 3:30 p.m. | St. Dominic at Greely | |
| 05/21/2019 | 4 p.m. | Van Buren at Madawaska | |
| 05/21/2019 | 4 p.m. | Windham at Cheverus | |
| 05/21/2019 | 3:30 p.m. | Yarmouth at York | |
| 05/22/2019 | 4 p.m. | Bangor at Skowhegan | |
| 05/22/2019 | 4 p.m. | Brunswick at Morse | |
| 05/22/2019 | 4 p.m. | Ellsworth at Mt. Desert Island | |
| 05/22/2019 | 4 p.m. | Fort Kent at Van Buren | |
| 05/22/2019 | 3:30 p.m. | Freeport at Yarmouth | |
| 05/22/2019 | 4 p.m. | Gorham at South Portland | |
| 05/22/2019 | 3:30 p.m. | Lake Region at Greely | |
| 05/22/2019 | 3:30 p.m. | Madawaska at Caribou | |
| 05/22/2019 | 4 p.m. | Maranacook at Morse | |
| 05/22/2019 | 4 p.m. | Mattanawcook Academy at Orono | |
| 05/22/2019 | 4 p.m. | Mountain Valley at Wiscasset | |
| 05/22/2019 | 4 p.m. | Spruce Mountain at Madison | |
| 05/22/2019 | 4 p.m. | Washington Academy at Old Town | |
| 05/22/2019 | 4 p.m. | Winthrop at Boothbay | |
| 05/22/2019 | 3:30 p.m. | Woodland at Calais | |
| 05/23/2019 | 2:30 p.m. | Bangor at Brewer | |
| 05/23/2019 | 4 p.m. | Hermon at Foxcroft Academy | |
| 05/23/2019 | 4 p.m. | Mt. Blue at Oxford Hills | |
| 05/23/2019 | 4 p.m. | Old Town at John Bapst | |
| 05/24/2019 | 4 p.m. | Edward Little at Mt. Blue | |
