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| All Sports |
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| Basketball - Girls | | 12.09.2023 – Winthrop 72, Boothbay Region 16 |
| 12.12.2023 – North Yarmouth Academy 45, Winthrop 42 |
| 12.21.2023 – Winthrop 44, Old Orchard Beach 41 |
| 12.27.2023 – Hall-Dale 72, Winthrop 19 |
| 1.02.2024 – Winthrop 55, Dirigo 29 |
| 1.05.2024 – Winthrop 59, Kents Hill 34 |
| 1.09.2024 – Winthrop 69, Waterville 45 |
| 1.12.2024 – Winthrop 55, Lisbon 13 |
| 1.18.2024 – Maranacook 35, Winthrop 32 |
| 1.20.2024 – Winthrop 58, Monmouth Academy 45 |
| 1.22.2024 – Winthrop 43, Traip Academy 22 |
6 pm 1.24.2024 – Madison at Winthrop |
6:30 pm 1.26.2024 – Winthrop at Mountain Valley |
2 pm 1.27.2024 – Winthrop at Waynflete |
6 pm 1.29.2024 – Mount Abram at Winthrop |
6 pm 1.31.2024 – Oak Hill at Winthrop |
6:30 pm 2.05.2024 – Winthrop at Spruce Mountain |
6:30 pm 2.07.2024 – Telstar at Winthrop |
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