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| All Schools |
| All Sports |
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| Field Hockey | | 9.01.2021 – Saint Dominic 4, Gray-New Gloucester 0 |
| 9.03.2021 – Fryeburg Academy 3, Gray-New Gloucester 0 |
| 9.07.2021 – Gray-New Gloucester 6, Traip Academy 0 |
| 9.11.2021 – Gray-New Gloucester 1, Sacopee Valley 0 |
| 9.17.2021 – York 7, Gray-New Gloucester 0 |
| 9.20.2021 – Cape Elizabeth 8, Gray-New Gloucester 0 |
| 9.27.2021 – Poland Regional 1, Gray-New Gloucester 0 |
| 10.01.2021 – Lake Region 5, Gray-New Gloucester 1 |
| 10.05.2021 – Gray-New Gloucester 3, Sacopee Valley 2 |
| 10.11.2021 – Freeport 5, Gray-New Gloucester 1 |
| 10.13.2021 – Cape Elizabeth 5, Gray-New Gloucester 0 |
| 10.18.2021 – Lake Region 4, Gray-New Gloucester 0 |
| 10.21.2021 – Freeport 6, Gray-New Gloucester 0 |
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