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| All Sports |
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| Football | | 9.02.2023 – Freeport 39, Hall-Dale/Winthrop/Maranacook 33 |
| 9.08.2023 – Hall-Dale/Winthrop/Maranacook 53, Maine Central Institute 47 |
| 9.16.2023 – Wells 41, Hall-Dale/Winthrop/Maranacook 0 |
| 9.23.2023 – Oak Hill 20, Hall-Dale/Winthrop/Maranacook 12 |
| 9.30.2023 – Hall-Dale/Winthrop/Maranacook 7, John Bapst 6 |
| 10.06.2023 – Hall-Dale/Winthrop/Maranacook 28, Poland Regional 8 |
| 10.13.2023 – Hall-Dale/Winthrop/Maranacook 21, Lisbon 0 |
| 10.20.2023 – Hall-Dale/Winthrop/Maranacook 42, Old Town 6 |
| 10.31.2023 – Hall-Dale/Winthrop/Maranacook 43, Lisbon 8 |
| 11.04.2023 – Hall-Dale/Winthrop/Maranacook 17, Oak Hill 14 |
| 11.10.2023 – Wells 35, Hall-Dale/Winthrop/Maranacook 6 |
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