| All Schools |
| |
| Field Hockey |
| 9.26.2020 – Saint Dominic 4, Gray-New Gloucester 0 |
| 9.29.2020 – Windham 5, Gray-New Gloucester 0 |
| 10.02.2020 – Greely 5, Gray-New Gloucester 1 |
| 10.05.2020 – Bonny Eagle 5, Gray-New Gloucester 0 |
| 10.14.2020 – Yarmouth 5, Gray-New Gloucester 0 |
| 10.19.2020 – Yarmouth 6, Gray-New Gloucester 0 |
| 10.26.2020 – Freeport 5, Gray-New Gloucester 1 |
| |
| Soccer - Boys |
| 9.26.2020 – Gray-New Gloucester 7, Poland Regional 0 |
| 9.30.2020 – Waynflete 6, Gray-New Gloucester 1 |
| 10.06.2020 – North Yarmouth Academy 1, Gray-New Gloucester 0 |
| 10.08.2020 – Gray-New Gloucester 4, Saint Dominic 0 |
| 10.14.2020 – Lake Region 4, Gray-New Gloucester 2 |
| 10.20.2020 – Lake Region 3, Gray-New Gloucester 1 |
| 10.22.2020 – Windham 4, Gray-New Gloucester 1 |
| 10.28.2020 – Gray-New Gloucester 2, Saint Dominic 1 |
| |
| Soccer - Girls |
| 9.26.2020 – Gray-New Gloucester 6, Poland Regional 0 |
| 9.30.2020 – Waynflete 1, Gray-New Gloucester 0 |
| 10.07.2020 – Bonny Eagle 5, Gray-New Gloucester 2 |
| 10.09.2020 – Gray-New Gloucester 3, Saint Dominic 1 |
| 10.14.2020 – North Yarmouth Academy 4, Gray-New Gloucester 0 |
| 10.15.2020 – Gray-New Gloucester 3, Lake Region 0 |
| 10.19.2020 – Windham 4, Gray-New Gloucester 0 |
| 10.28.2020 – Gray-New Gloucester 2, Saint Dominic 0 |
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