| • Games for All Schools in September, 2026 |
| |
| Football |
| 9.4.2026 – Winthrop 34, Lisbon 3 |
| 9.11.2026 – Freeport 29, Winthrop 28 |
| 9.17.2026 – Winthrop 38, Madison 8 |
| 9.24.2026 – Poland Regional at Winthrop |
7 pm |
| 9.24.2026 – Winthrop 34, Poland Regional 6 |
| |
| Soccer - Boys |
| 9.3.2026 – Winthrop 1, Oak Hill 1 |
| 9.10.2026 – Maranacook 1, Winthrop 0 |
| 9.12.2026 – Mountain Valley 3, Winthrop 2 |
| 9.14.2026 – Buckfield 6, Winthrop 1 |
| 9.16.2026 – Hall-Dale 5, Winthrop 0 |
| 9.18.2026 – Winthrop 4, Spruce Mountain 1 |
| 9.26.2026 – Winthrop 4, Mount Abram 3 |
| 9.29.2026 – Winthrop 3, Richmond 2 |
| |
| Soccer - Girls |
| 9.4.2026 – Oak Hill 3, Winthrop 1 |
| 9.7.2026 – Winthrop 7, Boothbay/Wiscasset 1 |
| 9.15.2026 – Hall-Dale at Winthrop |
4 pm |
| 9.15.2026 – Hall-Dale 4, Winthrop 0 |
| 9.17.2026 – Mount Abram 8, Winthrop 0 |
| 9.22.2026 – Winthrop 2, Lisbon 1 |
| 9.25.2026 – Winthrop 4, Telstar 0 |
| |
| Field Hockey |
| 9.8.2026 – Winthrop 10, Telstar 0 |
| 9.9.2026 – Winthrop 4, Oak Hill 0 |
| 9.11.2026 – Freeport 2, Winthrop 1 |
| 9.14.2026 – Winthrop 5, Dirigo 1 |
| 9.19.2026 – Winthrop 3, Spruce Mountain 2 |
| 9.23.2026 – Winthrop 2, Mountain Valley 1 |
| 9.25.2026 – Winthrop 3, Messalonskee 2 |
| 9.30.2026 – Winthrop 2, Boothbay Region 1 |
