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| All Sports |
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| Soccer - Boys | | 9.09.2023 – Spruce Mountain 10, Vinalhaven 0 |
| 9.18.2023 – Telstar 8, Vinalhaven 2 |
| 9.23.2023 – Rangeley 8, Vinalhaven 0 |
| 9.26.2023 – Buckfield 8, Vinalhaven 0 |
| 9.29.2023 – Shead 3, Vinalhaven 0 |
| 9.30.2023 – Shead 4, Vinalhaven 0 |
| 10.05.2023 – Searsport 7, Vinalhaven 0 |
| 10.09.2023 – Spruce Mountain 6, Vinalhaven 0 |
| 10.10.2023 – Temple 9, Vinalhaven 1 |
| 10.17.2023 – Pine Tree Academy 8, Vinalhaven 0 |
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