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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.07.2023 – Woodland 3, Jonesport-Beals 2 |
| 9.11.2023 – Narraguagus 5, Woodland 0 |
| 9.13.2023 – Lee Academy 7, Woodland 2 |
| 9.18.2023 – Sumner 4, Woodland 0 |
| 9.20.2023 – Lee Academy 5, Woodland 3 |
| 9.25.2023 – MSSM 3, Woodland 2 |
| 9.27.2023 – Woodland 2, Sumner 2 |
| 9.29.2023 – Woodland 2, Machias 1 |
| 10.03.2023 – Woodland 2, Jonesport-Beals 1 |
| 10.05.2023 – Calais 6, Woodland 0 |
| 10.12.2023 – Narraguagus 2, Woodland 0 |
| 10.14.2023 – Woodland 3, Washburn 0 |
| 10.16.2023 – Calais 0, Woodland 0 |
| 10.20.2023 – Katahdin 1, Woodland 0 |
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