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