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| Basketball - Boys | | 12.06.2019 – Fryeburg Academy 55, Gray-New Gloucester 43 |
| 12.10.2019 – Gray-New Gloucester 62, Mount Ararat 40 |
| 12.13.2019 – York 81, Gray-New Gloucester 65 |
| 12.18.2019 – Kennebunk 87, Gray-New Gloucester 62 |
| 12.20.2019 – Gray-New Gloucester 68, Poland Regional 56 |
| 1.02.2020 – Gray-New Gloucester 58, Freeport 50 |
| 1.04.2020 – Gray-New Gloucester 63, Yarmouth 57 |
| 1.07.2020 – Lake Region 49, Gray-New Gloucester 47 |
| 1.09.2020 – Greely 76, Gray-New Gloucester 68 |
| 1.11.2020 – Gray-New Gloucester 81, Freeport 66 |
| 1.14.2020 – Gray-New Gloucester 60, Yarmouth 41 |
| 1.17.2020 – Gray-New Gloucester 55, Cape Elizabeth 44 |
| 1.21.2020 – Gray-New Gloucester 68, Poland Regional 49 |
| 1.24.2020 – Gray-New Gloucester 70, Lake Region 56 |
| 1.28.2020 – Wells 70, Gray-New Gloucester 57 |
| 1.31.2020 – Greely 71, Gray-New Gloucester 63 |
| 2.04.2020 – Gray-New Gloucester 62, Fryeburg Academy 59 |
| 2.15.2020 – Kennebunk 86, Gray-New Gloucester 60 |
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