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| • Games for All Schools in May, 2024 |
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| Baseball |
| 5.1.2024 – Lawrence 19, Winslow 1 |
| 5.3.2024 – Boothbay/Wiscasset 15, Winslow 1 |
| 5.3.2024 – Boothbay Region at Winslow |
4 pm |
| 5.6.2024 – Belfast 4, Winslow 1 |
| 5.8.2024 – Oceanside 6, Winslow 2 |
| 5.13.2024 – Cony 9, Winslow 0 |
| 5.17.2024 – Lawrence 12, Winslow 1 |
| 5.20.2024 – Nokomis 6, Winslow 1 |
| 5.22.2024 – Mount View 10, Winslow 0 |
| 5.24.2024 – Waterville 8, Winslow 0 |
| 5.28.2024 – Erskine Academy 10, Winslow 0 |
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| Softball |
| 5.1.2024 – Lawrence 10, Winslow 2 |
| 5.3.2024 – Hall-Dale 7, Winslow 4 |
| 5.6.2024 – Belfast 14, Winslow 5 |
| 5.8.2024 – Oceanside 8, Winslow 5 |
| 5.13.2024 – Cony 19, Winslow 5 |
| 5.17.2024 – Lawrence 14, Winslow 2 |
| 5.20.2024 – Nokomis 11, Winslow 0 |
| 5.22.2024 – Mount View 13, Winslow 3 |
| 5.24.2024 – Winslow 21, Waterville 1 |
| 5.28.2024 – Erskine Academy 13, Winslow 6 |
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