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| All Schools |
| All Sports |
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| Basketball - Boys | | 12.08.2023 – Winthrop 51, Boothbay Region 36 |
| 12.12.2023 – Winthrop 60, North Yarmouth Academy 34 |
| 12.21.2023 – Old Orchard Beach 50, Winthrop 45 |
| 12.28.2023 – Winthrop 55, Hall-Dale 53 |
| 1.02.2024 – Dirigo 54, Winthrop 48 |
| 1.06.2024 – Winthrop 59, Lisbon 43 |
| 1.09.2024 – Winthrop 34, Waterville 30 |
| 1.11.2024 – Maranacook 70, Winthrop 50 |
| 1.13.2024 – Mountain Valley 60, Winthrop 48 |
| 1.15.2024 – Winthrop 46, Old Orchard Beach 35 |
| 1.17.2024 – Monmouth Academy 54, Winthrop 46 |
6:30 pm 1.19.2024 – Winthrop at Madison |
6 pm 1.22.2024 – Winthrop at Traip Academy |
6:30 pm 1.25.2024 – Winthrop at Mount Abram |
2:30 pm 1.27.2024 – Waynflete at Winthrop |
6:30 pm 2.02.2024 – Winthrop at Oak Hill |
6:30 pm 2.06.2024 – Spruce Mountain at Winthrop |
6:30 pm 2.08.2024 – Winthrop at Telstar/Gould |
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