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| All Schools |
| All Sports |
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| Softball | | 4.22.2026 – Narraguagus 8, Woodland 2 |
4 pm 4.25.2026 – Jonesport-Beals at Woodland |
| 4.29.2026 – Machias 6, Woodland 5 |
1 pm 5.02.2026 – Calais at Woodland |
| 5.05.2026 – Narraguagus 9, Woodland 5 |
4 pm 5.06.2026 – Narraguagus at Woodland |
| 5.08.2026 – Woodland 24, Searsport 14 |
| 5.09.2026 – Woodland 17, Calais 2 |
| 5.11.2026 – Woodland 19, Shead 2 |
| 5.13.2026 – Woodland 13, Bangor Christian 12 |
| 5.18.2026 – Machias 8, Woodland 6 |
| 5.21.2026 – Penobscot Valley 17, Woodland 7 |
| 5.22.2026 – Woodland 14, Calais 3 |
12 pm 5.25.2026 – Woodland at Jonesport-Beals |
| 5.26.2026 – Woodland 17, Shead 4 |
| 5.30.2026 – Woodland 9, Jonesport-Beals 6 |
4 pm 6.01.2026 – Penobscot Valley at Woodland |
3:30 pm 6.02.2026 – Woodland at Searsport |
4 pm 6.03.2026 – Woodland at Bangor Christian |
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