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| All Sports |
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| Soccer - Boys | | 9.03.2021 – Gray-New Gloucester 5, Wells 0 |
| 9.07.2021 – Gray-New Gloucester 6, Lake Region 1 |
| 9.14.2021 – Gray-New Gloucester 7, Poland Regional 0 |
| 9.17.2021 – York 2, Gray-New Gloucester 0 |
| 9.23.2021 – Freeport 1, Gray-New Gloucester 0 |
| 10.02.2021 – Yarmouth 7, Gray-New Gloucester 1 |
| 10.05.2021 – Gray-New Gloucester 6, Wells 0 |
| 10.08.2021 – North Yarmouth Academy 0, Gray-New Gloucester 0 |
7 PM 10.12.2021 – Gray-New Gloucester at Cape Elizabeth |
| 10.14.2021 – Gray-New Gloucester 6, Lake Region 3 |
| 10.18.2021 – Gray-New Gloucester 1, Poland Regional 0 |
6 PM 10.19.2021 – Poland Regional at Gray-New Gloucester |
| 10.22.2021 – Cape Elizabeth 3, Gray-New Gloucester 0 |
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