| Wed, Sep 8 | SMAA: Scarborough, South Portland, Thornton, SMAA: Scarborou | Marshwood HS | South Berwick, ME | | | |
| Fri, Sep 17 | SMAA: Marshwood, Portland @ Windham | Windham HS | Windham, ME | | | |
| Sat, Sep 25 | Southwest Classic | Twin Brook Recreation Center | Cumberland, ME | | | |
| Wed, Sep 29 | SMAA: Marshwood, Gorham @ McAuley | Catherine McAuley HS | Portland, ME | | | |
| Sat, Oct 2 | Festival of Champions | Troy Howard MS | Belfast, ME | | | |
| Fri, Oct 8 | Scarborough, Cheverus, Marshwood | Scarborough HS | Scarborough, ME | | | |
| Sat, Oct 23 | Western Maine Regional Championships | Twin Brook Recreation Center | Cumberland, ME | | | |
| Sat, Oct 30 | Maine Class A State Cross Country Championships | Troy Howard MS | Belfast, ME | | | |
