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| All Schools |
| All Sports |
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| Soccer - Girls | | 9.06.2023 – Woodland 12, East Grand 0 |
| 9.08.2023 – Mattanawcook Academy 7, Woodland 0 |
| 9.13.2023 – Woodland 4, Calais 1 |
| 9.21.2023 – Woodland 2, Shead 1 |
| 9.23.2023 – Bangor Christian 3, Woodland 1 |
| 9.25.2023 – Woodland 5, Narraguagus 0 |
| 9.29.2023 – Penobscot Valley 10, Woodland 0 |
| 10.02.2023 – Woodland 8, East Grand 0 |
| 10.05.2023 – Shead 2, Woodland 1 |
| 10.06.2023 – Bangor Christian 3, Woodland 0 |
| 10.11.2023 – Woodland 3, Narraguagus 0 |
| 10.14.2023 – Central Aroostook 10, Woodland 0 |
| 10.17.2023 – Woodland 4, Calais 0 |
| 10.20.2023 – Fort Fairfield 3, Woodland 2 |
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