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| All Sports |
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| Soccer - Boys | | 9.05.2023 – Caribou 4, Old Town 1 |
| 9.09.2023 – Hermon 4, Old Town 3 |
| 9.13.2023 – Old Town 2, Orono 0 |
| 9.15.2023 – Ellsworth 4, Old Town 0 |
| 9.20.2023 – Old Town 1, Presque Isle 1 |
| 9.23.2023 – Caribou 3, Old Town 0 |
| 9.27.2023 – Mount Desert Island 1, Old Town 0 |
| 9.30.2023 – Old Town 6, Hermon 2 |
| 10.03.2023 – Ellsworth 4, Old Town 2 |
| 10.05.2023 – Old Town 0, Mount Desert Island 0 |
| 10.09.2023 – Presque Isle 1, Old Town 0 |
| 10.11.2023 – Old Town 1, Presque Isle 1 |
| 10.11.2023 – Old Town 5, Orono 1 |
| 10.16.2023 – John Bapst 6, Old Town 2 |
| 10.20.2023 – Gardiner 4, Old Town 0 |
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