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| All Schools |
| All Sports |
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| Baseball | 1 pm 4.24.2026 – Winslow at Cony |
| 4.27.2026 – Nokomis 16, Winslow 3 |
| 5.01.2026 – Oceanside 15, Winslow 4 |
| 5.04.2026 – Lawrence 9, Winslow 0 |
| 5.05.2026 – Waterville 14, Winslow 4 |
| 5.08.2026 – Lawrence 19, Winslow 7 |
10 am 5.09.2026 – Winslow at Cony |
| 5.11.2026 – Gardiner 17, Winslow 1 |
| 5.13.2026 – Leavitt 8, Winslow 0 |
4 pm 5.15.2026 – Erskine Academy at Winslow |
| 5.18.2026 – Nokomis 10, Winslow 0 |
| 5.20.2026 – Maine Central Institute 14, Winslow 12 |
| 5.21.2026 – Cony 20, Winslow 0 |
4 pm 5.22.2026 – Winslow at Belfast |
5 pm 5.25.2026 – Erskine Academy at Winslow |
4 pm 5.26.2026 – Winslow at Oceanside |
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