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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.12.2026 – Vinalhaven/North Haven 4, Dirigo 2 |
5 pm 9.25.2026 – Greenville at Vinalhaven/North Haven |
| 9.25.2026 – Vinalhaven/North Haven 1, Greenville 1 |
| 9.26.2026 – Carrabec/Madison Co-op 2, Vinalhaven/North Haven 0 |
| 9.28.2026 – Vinalhaven/North Haven 1, Boothbay/Wiscasset 1 |
| 10.01.2026 – Pine Tree Academy 5, Vinalhaven/North Haven 0 |
| 10.03.2026 – Telstar 6, Vinalhaven/North Haven 0 |
| 10.08.2026 – Valley 1, Vinalhaven/North Haven 1 |
11:30 am 10.10.2026 – Vinalhaven/North Haven at Islesboro |
| 10.12.2026 – Vinalhaven/North Haven 2, Rangeley 1 |
11 am 10.15.2026 – Islesboro at Vinalhaven/North Haven |
| 10.20.2026 – Temple 3, Vinalhaven/North Haven 2 |
| 10.21.2026 – Islesboro 2, Vinalhaven/North Haven 1 |
12 pm 10.27.2026 – Vinalhaven/North Haven at Telstar |
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