| 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, Massabesic, Massabesic, Massabesic, South Portland, South Portland, South Portland, Cheverus, Cheverus, Cheverus | 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 | Bonny Eagle, Sanford, Portland | Peterson Field, Scarborough, ME |
| 09/04/2026 | 4:30 PM | League | Mt. Blue | Gardiner Area, Leavitt Area, Lawrence, Cony HS, Waterville | Mt. Blue Cross Country Course |
| 09/05/2026 | 10:00 AM | League | Windham | Deering, Biddeford, Noble | 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 | Dexter Regional, Searsport HS, Central, George Stevens Academy, Sumner Memorial, Mattanawcook Academy/Lee/Penobscot Valley Coop, Washington Academy, Mia Mills | Bucksport |
| 09/17/2026 | 4:00 PM | League | Thornton Academy | Scarborough, South Portland, Noble | Thornton Academy |
| 09/18/2026 | 4:00 PM | League | Central | BCS/PCS, Old Town, Mattanawcook Academy/Lee/Penobscot Valley Coop, Orono, Schenck/Stearns Coop | Central |
| 09/18/2026 | 4:00 PM | League | Gorham | Cheverus, Portland, Marshwood, Biddeford | 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 | York, Lake Region, Fryeburg Academy, Gray-New Gloucester | Minot Community Park |
| 09/19/2026 | 10:30 AM | League | Brunswick | Waterville, Messalonskee, Lewiston, Mt. Ararat, Edward Little | Brunswick High School |
| 09/19/2026 | 12:00 PM | League | Skowhegan Area | Leavitt Area, Lawrence, Gardiner Area, Oxford Hills, 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, Mt. Ararat, Maine Central Institute, Edward Little | @ Roberts Farm - Norway |
| 09/25/2026 | 4:00 PM | League | Biddeford | Massabesic, Scarborough, Westbrook | TBA |
| 09/25/2026 | 4:00 PM | League | South Portland | Marshwood, Windham, Cheverus, Bonny Eagle | 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 | Wells, Traip Academy | Minot Community Park |
| 10/03/2026 | | League | Belfast Area | Scarborough | Belfast Middle School |
| 10/07/2026 | 3:45 PM | League | Deering | Biddeford, Kennebunk, Thornton Academy | Deering H.S. (XC Course/SOC Fields) |
| 10/08/2026 | 4:30 PM | League | Cape Elizabeth | Greely, Traip Academy | Gull Crest Fields |
| 10/08/2026 | 5:00 PM | League | Gray-New Gloucester | Waynflete, Poland Regional, Wells | 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 | Lewiston, Oceanside, Bangor, Waterville, Morse, Brewer, Belfast Area, Oxford Hills, Brunswick, Skowhegan Area, Edward Little, Leavitt Area, Maine Central Institute, Cony HS, Lincoln Academy, Erskine Academy, Gardiner Area, Mt. Ararat | Mt. Blue Cross Country Course |
| 10/09/2026 | 4:00 PM | League | Cheverus | Bonny Eagle, South Portland, Westbrook | 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 |