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| All Schools |
| All Sports |
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| Field Hockey | | 8.31.2023 – Old Town 1, Hermon 0 |
| 9.06.2023 – Dexter/Central 1, Old Town 0 |
| 9.08.2023 – Old Town 3, Hampden Academy 2 |
| 9.11.2023 – Old Town 3, Schenck/Stearns 0 |
| 9.14.2023 – Orono 3, Old Town 2 |
| 9.19.2023 – Old Town 2, Piscataquis 0 |
| 9.20.2023 – Orono 1, Old Town 0 |
| 9.26.2023 – Old Town 2, John Bapst 1 |
| 9.29.2023 – Brewer 2, Old Town 0 |
| 10.03.2023 – Old Town 3, Hermon 2 |
| 10.07.2023 – Bangor 1, Old Town 0 |
| 10.12.2023 – Erskine Academy 2, Old Town 1 |
| 10.14.2023 – John Bapst 3, Old Town 1 |
| 10.17.2023 – Old Town 2, Mattanawcook/Lee 1 |
| 10.24.2023 – Cony 6, Old Town 0 |
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