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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.04.2026 – Searsport 3, Islesboro 1 |
| 9.08.2026 – Boothbay/Wiscasset 4, Islesboro 1 |
| 9.10.2026 – Pine Tree Academy 8, Islesboro 0 |
| 9.19.2026 – Greenville 5, Islesboro 1 |
| 9.22.2026 – Dirigo 5, Islesboro 4 |
| 9.24.2026 – Rangeley 2, Islesboro 0 |
TBA 9.24.2026 – Rangeley at Islesboro |
| 9.26.2026 – Valley 1, Islesboro 1 |
| 10.06.2026 – Searsport 3, Islesboro 2 |
| 10.08.2026 – Telstar 10, Islesboro 2 |
11:30 am 10.10.2026 – Vinalhaven/North Haven at Islesboro |
11 am 10.15.2026 – Islesboro at Vinalhaven/North Haven |
| 10.17.2026 – Carrabec/Madison Co-op 7, Islesboro 2 |
| 10.19.2026 – Temple 3, Islesboro 1 |
| 10.21.2026 – Islesboro 2, Vinalhaven/North Haven 1 |
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