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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.08.2026 – Bangor Christian 4, Woodland 0 |
| 9.10.2026 – GSA/Deer Isle-Ston. 8, Woodland 0 |
| 9.12.2026 – Narraguagus 3, Woodland 2 |
| 9.16.2026 – Central Aroostook 6, Woodland 2 |
| 9.18.2026 – Woodland 2, Penobscot Valley 1 |
| 9.24.2026 – Machias 1, Woodland 0 |
| 9.30.2026 – Woodland 2, Bangor Christian 1 |
| 10.05.2026 – Woodland 4, Penobscot Valley 1 |
| 10.06.2026 – GSA/Deer Isle-Ston. 6, Woodland 2 |
| 10.08.2026 – Woodland 6, Machias 0 |
| 10.12.2026 – Narraguagus 4, Woodland 1 |
3:30 pm 10.16.2026 – Central Aroostook at Woodland |
1 pm 10.17.2026 – Narraguagus at Woodland |
| 10.17.2026 – Central Aroostook 2, Woodland 0 |
| 10.19.2026 – Woodland 5, Machias 1 |
| 10.20.2026 – Narraguagus 3, Woodland 2 |
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