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| All Sports |
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| Soccer - Boys | | 9.07.2023 – Buckfield 2, Islesboro 1 |
| 9.12.2023 – Islesboro 5, Chop Point 0 |
| 9.14.2023 – Islesboro 1, Saint Dominic 1 |
| 9.16.2023 – Richmond 3, Islesboro 0 |
| 9.19.2023 – Islesboro 6, Searsport 0 |
| 9.21.2023 – Islesboro 6, Temple 1 |
| 9.28.2023 – Saint Dominic 2, Islesboro 1 |
| 9.29.2023 – Islesboro 2, Chop Point 1 |
| 10.02.2023 – Islesboro 3, Searsport 0 |
| 10.05.2023 – Islesboro 2, Chop Point 0 |
| 10.06.2023 – Islesboro 3, Temple 0 |
| 10.10.2023 – Buckfield 4, Islesboro 1 |
| 10.11.2023 – Islesboro 3, Pine Tree Academy 1 |
| 10.13.2023 – Richmond 2, Islesboro 0 |
| 10.24.2023 – Islesboro 2, Pine Tree Academy 1 |
| 11.02.2023 – Richmond 5, Islesboro 1 |
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