| All Schools |
| |
| Field Hockey |
10 am 8.29.2026 – Winslow at Brewer |
4 pm 9.01.2026 – Oak Hill at Winslow |
| 9.05.2026 – Winslow 5, Morse 1 |
| 9.08.2026 – Gardiner 7, Winslow 0 |
| 9.11.2026 – Hall-Dale/Monmouth 2, Winslow 1 |
| 9.15.2026 – Winslow 12, Oceanside 0 |
| 9.18.2026 – Winslow 2, Cony 2 |
| 9.22.2026 – Leavitt 7, Winslow 0 |
| 9.23.2026 – Leavitt 7, Winslow 0 |
| 9.25.2026 – Winslow 3, Lincoln Academy 0 |
4:30 pm 9.28.2026 – Winslow at Maine Central Institute |
| 10.01.2026 – Maine Central Institute 3, Winslow 1 |
| 10.03.2026 – Winslow 3, Erskine Academy 2 |
| 10.06.2026 – Winslow 2, Lawrence 0 |
| 10.08.2026 – Belfast 5, Winslow 1 |
| 10.13.2026 – Winslow 2, Erskine Academy 1 |
| 10.15.2026 – Nokomis 5, Winslow 0 |
| 10.19.2026 – Winslow 7, Waterville 1 |
| 10.27.2026 – Schenck/Stearns 2, Winslow 0 |
| |
| Football |
7 pm 8.28.2026 – Winslow at Messalonskee |
| 9.04.2026 – Wells 14, Winslow 13 |
| 9.11.2026 – Winslow 26, John Bapst/Bangor Christian/Ce 6 |
| 9.19.2026 – Winslow 46, Oak Hill 6 |
| 9.26.2026 – Winslow 14, Freeport 6 |
| 10.02.2026 – Winslow 44, Mattanawcook Academy 0 |
| 10.09.2026 – Winslow 38, Maine Central Institute 6 |
| 10.17.2026 – Winslow 30, Morse 6 |
| 10.24.2026 – Winslow 50, Madison 18 |
| |
| Soccer - Boys |
3:30 pm 8.28.2026 – Maranacook at Winslow |
5:30 pm 9.01.2026 – Ellsworth at Winslow |
| 9.04.2026 – Winslow 6, Medomak Valley 2 |
| 9.08.2026 – Leavitt 5, Winslow 2 |
| 9.11.2026 – Winslow 3, Central 0 |
| 9.14.2026 – Winslow 2, Maine Central Institute 0 |
| 9.17.2026 – Mount View 2, Winslow 1 |
| 9.19.2026 – Winslow 1, Waterville 0 |
| 9.24.2026 – Winslow 3, Mount View 2 |
3:30 pm 9.29.2026 – Maine Central Institute at Winslow |
| 9.30.2026 – Maine Central Institute 4, Winslow 1 |
| 10.01.2026 – Winslow 6, Central 1 |
| 10.06.2026 – Winslow 3, Waterville 0 |
| 10.08.2026 – Mount Abram 3, Winslow 1 |
| 10.10.2026 – Hall-Dale 5, Winslow 0 |
| 10.13.2026 – Winslow 4, Lawrence 1 |
| 10.15.2026 – Leavitt 6, Winslow 0 |
| 10.27.2026 – Mount View 4, Winslow 2 |
| |
| Soccer - Girls |
3:30 pm 8.26.2026 – Winslow at Belfast |
3:30 pm 9.01.2026 – Ellsworth at Winslow |
| 9.04.2026 – Winslow 5, Medomak Valley 0 |
| 9.08.2026 – Leavitt 3, Winslow 2 |
| 9.11.2026 – Central 2, Winslow 1 |
| 9.14.2026 – Winslow 7, Maine Central Institute 1 |
| 9.17.2026 – Winslow 3, Mount View 0 |
| 9.19.2026 – Winslow 5, Waterville 0 |
| 9.22.2026 – Winslow 5, Maine Central Institute 0 |
| 9.29.2026 – Winslow 4, Waterville 1 |
| 10.01.2026 – Winslow 5, Central 0 |
| 10.08.2026 – Mount Abram 1, Winslow 0 |
| 10.10.2026 – Hall-Dale 1, Winslow 0 |
| 10.13.2026 – Winslow 3, Lawrence 0 |
| 10.15.2026 – Leavitt 1, Winslow 1 |
| 10.17.2026 – Winslow 2, Mount View 0 |
| 10.27.2026 – Winslow 1, Mattanawcook Academy 0 |
| 10.29.2026 – Orono 1, Winslow 0 |
TBA 10.30.2026 – Winslow at Orono |
