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| All Schools |
| All Sports |
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| 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 |
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