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| All Schools |
| All Sports |
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| Soccer - Boys | | 8.31.2023 – Freeport 2, Gray-New Gloucester 1 |
| 9.06.2023 – Yarmouth 7, Gray-New Gloucester 0 |
| 9.08.2023 – Gray-New Gloucester 3, Leavitt 0 |
| 9.12.2023 – Gray-New Gloucester 5, Poland Regional 4 |
| 9.19.2023 – Gray-New Gloucester 1, Wells 0 |
| 9.21.2023 – Fryeburg Academy 4, Gray-New Gloucester 1 |
| 9.23.2023 – Gray-New Gloucester 6, North Yarmouth Academy 1 |
| 9.26.2023 – Cape Elizabeth 5, Gray-New Gloucester 0 |
| 9.30.2023 – Gray-New Gloucester 0, Waynflete 0 |
| 10.02.2023 – Gray-New Gloucester 7, Lake Region 2 |
| 10.04.2023 – Lincoln Academy 5, Gray-New Gloucester 0 |
| 10.05.2023 – Poland Regional 1, Gray-New Gloucester 1 |
| 10.10.2023 – Greely 5, Gray-New Gloucester 0 |
| 10.17.2023 – York 3, Gray-New Gloucester 1 |
| 10.20.2023 – Fryeburg Academy 3, Gray-New Gloucester 1 |
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