| GameDate | Time | Type | Home School | Away School | Site |
| 09/03/2026 | 4:00 PM | League | Edward Little | Oxford Hills | @ Auburn MS |
| 09/03/2026 | 4:00 PM | League | Kennebunk | Cheverus, Cheverus, Cheverus, Gorham, Gorham, Gorham, Massabesic, Massabesic, Massabesic, South Portland, South Portland, South Portland | Kennebunk Elementary School |
| 09/03/2026 | 4:30 PM | League | Wells | Western Maine Conference League, Poland Regional | Laudholm Farm |
| 09/04/2026 | 4:00 PM | League | Scarborough | Portland, Sanford, Bonny Eagle | Peterson Field, Scarborough, ME |
| 09/04/2026 | 4:30 PM | League | Mt. Blue | Lawrence, Leavitt Area, Waterville, Gardiner Area, Cony HS | Mt. Blue Cross Country Course |
| 09/05/2026 | 10:00 AM | League | Windham | Biddeford, Noble, Deering | Windham High School |
| 09/12/2026 | 10:00 AM | League | Gorham | Poland Regional, Scarborough | Gorham Middle School |
| 09/12/2026 | 10:00 AM | League | Gorham | | Narragansett School |
| 09/12/2026 | 11:00 AM | League | Bucksport | George Stevens Academy, Dexter Regional, Sumner Memorial, Washington Academy, Mattanawcook Academy/Lee/Penobscot Valley Coop, Searsport HS, Mia Mills, Central | Bucksport |
| 09/17/2026 | 4:00 PM | League | Thornton Academy | Scarborough, South Portland, Noble | Thornton Academy |
| 09/18/2026 | 4:00 PM | League | Central | Orono, Schenck/Stearns Coop, BCS/PCS, Old Town, Mattanawcook Academy/Lee/Penobscot Valley Coop | Central |
| 09/18/2026 | 4:00 PM | League | Gorham | Marshwood, Cheverus, Biddeford, Portland | Narragansett School |
| 09/18/2026 | 4:00 PM | League | Westbrook | Sanford, Windham, Kennebunk | Smiling Hill Farm |
| 09/18/2026 | 5:00 PM | League | Poland Regional | Fryeburg Academy, Lake Region, York, Gray-New Gloucester | Minot Community Park |
| 09/19/2026 | 10:30 AM | League | Brunswick | Mt. Ararat, Waterville, Edward Little, Messalonskee, Lewiston | Brunswick High School |
| 09/19/2026 | 12:00 PM | League | Skowhegan Area | Leavitt Area, Winslow, Oxford Hills, Lawrence, Gardiner Area | Skowhegan Area High School |
| 09/22/2026 | 4:00 PM | League | Calais | | Moosehorn Wildlife Refuge |
| 09/25/2026 | 4:00 PM | League | Oxford Hills | Edward Little, Leavitt Area, Mt. Ararat, Maine Central Institute | @ Roberts Farm - Norway |
| 09/25/2026 | 4:00 PM | League | Biddeford | Scarborough, Massabesic, Westbrook | TBA |
| 09/25/2026 | 4:00 PM | League | South Portland | Cheverus, Marshwood, Bonny Eagle, Windham | Wainwright Flds |
| 09/25/2026 | 5:00 PM | League | Traip Academy | Greely, Waynflete, Maine Coast Waldorf | Fort Foster |
| 09/25/2026 | 5:00 PM | League | Lake Region | Poland Regional | Lake Region High School |
| 10/02/2026 | 4:30 PM | League | Poland Regional | Traip Academy, Wells | Minot Community Park |
| 10/03/2026 | | League | Belfast Area | Scarborough | Belfast Middle School |
| 10/07/2026 | 3:45 PM | League | Deering | Kennebunk, Thornton Academy, Biddeford | Deering H.S. (XC Course/SOC Fields) |
| 10/08/2026 | 4:30 PM | League | Cape Elizabeth | Traip Academy, Greely | Gull Crest Fields |
| 10/08/2026 | 5:00 PM | League | Gray-New Gloucester | Waynflete, Wells, Poland Regional | Gray-New Gloucester High School |
| 10/09/2026 | 4:00 PM | League | Portland | Windham, Scarborough, Gorham, Falmouth | Eastern Prom Portland |
| 10/09/2026 | 4:00 PM | League | Massabesic | Noble, Sanford, Marshwood | Giles Orchard |
| 10/09/2026 | 4:00 PM | League | Mt. Blue | Brewer, Morse, Erskine Academy, Lewiston, Lincoln Academy, Skowhegan Area, Mt. Ararat, Cony HS, Bangor, Oceanside, Edward Little, Leavitt Area, Oxford Hills, Belfast Area, Gardiner Area, Waterville, Brunswick, Maine Central Institute | Mt. Blue Cross Country Course |
| 10/09/2026 | 4:00 PM | League | Cheverus | Bonny Eagle, Westbrook, South Portland | TBA |
| 10/15/2026 | 4:00 PM | League | Lake Region | Poland Regional, Western Maine Conference League | Lake Region High School |
| 10/17/2026 | 10:00 AM | League | Sanford | Scarborough | Sanford High School |
| 10/17/2026 | 11:00 AM | Postseason | Cony HS | Oxford Hills | @ Cony HS |