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| All Sports |
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| Softball | | 4.29.2026 – Oak Hill 18, Winthrop/Kents Hill 1 |
4 pm 5.01.2026 – Cony at Winthrop/Kents Hill |
| 5.04.2026 – Madison 11, Winthrop/Kents Hill 1 |
4 pm 5.06.2026 – Mount Abram at Winthrop/Kents Hill |
| 5.08.2026 – Old Orchard Beach 14, Winthrop/Kents Hill 4 |
| 5.11.2026 – Dirigo 16, Winthrop/Kents Hill 0 |
| 5.13.2026 – Maine Central Institute 12, Winthrop/Kents Hill 10 |
| 5.16.2026 – Cony 18, Winthrop/Kents Hill 1 |
| 5.19.2026 – Spruce Mountain 14, Winthrop/Kents Hill 1 |
| 5.20.2026 – Monmouth Academy 20, Winthrop/Kents Hill 4 |
| 5.22.2026 – Winthrop/Kents Hill 15, Mount Abram 4 |
| 5.22.2026 – Winthrop/Kents Hill 13, Mount Abram 12 |
| 5.25.2026 – Lisbon 16, Winthrop/Kents Hill 0 |
| 5.27.2026 – Winthrop/Kents Hill 15, Maranacook 2 |
| 5.28.2026 – Winthrop/Kents Hill 16, Maine Central Institute 9 |
| 5.30.2026 – Lisbon 16, Winthrop/Kents Hill 0 |
| 6.01.2026 – Mountain Valley 10, Winthrop/Kents Hill 0 |
| 6.03.2026 – Winthrop/Kents Hill 16, Hall-Dale 10 |
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