| All Schools |
| |
| Field Hockey |
| 9.05.2019 – Gray-New Gloucester 7, Traip Academy 0 |
| 9.10.2019 – Lake Region 6, Gray-New Gloucester 1 |
| 9.11.2019 – Gray-New Gloucester 2, Cape Elizabeth 1 |
| 9.17.2019 – Greely 2, Gray-New Gloucester 1 |
| 9.19.2019 – Gray-New Gloucester 5, North Yarmouth Academy 0 |
| 9.23.2019 – Yarmouth 2, Gray-New Gloucester 0 |
| 9.25.2019 – Saint Dominic 2, Gray-New Gloucester 0 |
| 9.27.2019 – Fryeburg Academy 4, Gray-New Gloucester 1 |
| 10.03.2019 – Poland Regional 2, Gray-New Gloucester 1 |
| 10.09.2019 – Fryeburg Academy 3, Gray-New Gloucester 0 |
| 10.11.2019 – Gray-New Gloucester 4, Sacopee Valley 0 |
| 10.15.2019 – Cape Elizabeth 3, Gray-New Gloucester 1 |
| 10.18.2019 – York 5, Gray-New Gloucester 1 |
| |
| Football |
| 9.06.2019 – Mount Ararat 56, Gray-New Gloucester 28 |
| 9.13.2019 – Gray-New Gloucester 50, Ellsworth/Sumner 44 |
| 9.20.2019 – Telstar 54, Gray-New Gloucester 42 |
| 9.27.2019 – Maranacook 46, Gray-New Gloucester 26 |
| 10.04.2019 – Yarmouth 64, Gray-New Gloucester 36 |
| 10.12.2019 – Mount Ararat 36, Gray-New Gloucester 28 |
| 10.19.2019 – Old Orchard Beach 50, Gray-New Gloucester 22 |
06:00 PM 10.25.2019 – Ellsworth/Sumner at Gray-New Gloucester |
| |
| Soccer - Boys |
| 9.05.2019 – Freeport 5, Gray-New Gloucester 0 |
| 9.10.2019 – Gray-New Gloucester 6, Lake Region 0 |
| 9.14.2019 – Gray-New Gloucester 4, Poland Regional 1 |
| 9.18.2019 – York 1, Gray-New Gloucester 1 |
| 9.21.2019 – Gray-New Gloucester 8, Wells 1 |
| 9.24.2019 – Greely 2, Gray-New Gloucester 1 |
| 9.26.2019 – Gray-New Gloucester 4, Fryeburg Academy 2 |
| 10.03.2019 – Gray-New Gloucester 9, Sacopee Valley 1 |
| 10.05.2019 – Waynflete 6, Gray-New Gloucester 0 |
| 10.10.2019 – Gray-New Gloucester 5, Saint Dominic 2 |
| 10.15.2019 – Yarmouth 1, Gray-New Gloucester 1 |
| 10.19.2019 – Greely 1, Gray-New Gloucester 0 |
06:00 PM 10.22.2019 – Gray-New Gloucester at Cape Elizabeth |
| |
| Soccer - Girls |
| 9.05.2019 – Freeport 2, Gray-New Gloucester 0 |
| 9.14.2019 – Gray-New Gloucester 3, Poland Regional 0 |
| 9.17.2019 – York 5, Gray-New Gloucester 1 |
| 9.21.2019 – Cape Elizabeth 3, Gray-New Gloucester 0 |
| 9.26.2019 – Gray-New Gloucester 8, Fryeburg Academy 2 |
| 9.28.2019 – Gray-New Gloucester 2, Wells 0 |
| 9.30.2019 – Gray-New Gloucester 4, Old Orchard Beach 1 |
| 10.03.2019 – Yarmouth 5, Gray-New Gloucester 1 |
| 10.05.2019 – Gray-New Gloucester 1, Waynflete 0 |
| 10.07.2019 – Traip Academy 2, Gray-New Gloucester 0 |
| 10.09.2019 – Gray-New Gloucester 2, Saint Dominic 0 |
| 10.15.2019 – Yarmouth 2, Gray-New Gloucester 1 |
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