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| All Sports |
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| Baseball | | 4.21.2025 – Waterville 4, Winslow 1 |
4 pm 4.22.2025 – Winslow at Waterville |
4 pm 4.25.2025 – Belfast at Winslow |
4 pm 4.28.2025 – Winslow at Oceanside |
| 4.30.2025 – Winslow 22, Maine Central Institute 9 |
4 pm 5.02.2025 – Nokomis at Winslow |
| 5.05.2025 – Lisbon 10, Winslow 0 |
4 pm 5.07.2025 – Winslow at Lawrence |
| 5.12.2025 – Belfast 12, Winslow 0 |
| 5.14.2025 – Oceanside 15, Winslow 3 |
| 5.15.2025 – Lawrence 10, Winslow 0 |
| 5.19.2025 – Cony 10, Winslow 0 |
| 5.20.2025 – Nokomis 15, Winslow 4 |
4 pm 5.23.2025 – Lawrence at Winslow |
1 pm 5.26.2025 – Winslow at Nokomis |
| 5.27.2025 – Nokomis 8, Winslow 2 |
4 pm 5.28.2025 – Mount View at Winslow |
| 5.30.2025 – Waterville 7, Winslow 1 |
11:30 am 5.31.2025 – Lawrence at Winslow |
4 pm 6.03.2025 – Winslow at Erskine Academy |
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