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| All Sports |
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| Football | | 9.01.2023 – Winslow 25, Old Town 7 |
| 9.08.2023 – Poland Regional 16, Old Town 0 |
| 9.15.2023 – Belfast 14, Old Town 7 |
| 9.22.2023 – John Bapst 31, Old Town 6 |
| 9.29.2023 – Hampden Academy 42, Old Town 13 |
| 10.06.2023 – Hermon 34, Old Town 0 |
| 10.13.2023 – Old Town 6, Madison 0 |
| 10.20.2023 – Hall-Dale/Winthrop/Maranacook 42, Old Town 6 |
| 10.31.2023 – Old Town 14, Belfast 12 |
| 11.04.2023 – John Bapst 28, Old Town 14 |
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