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| All Schools |
| All Sports |
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| Football | | 9.01.2023 – Leavitt 45, Fryeburg Academy 8 |
| 9.08.2023 – Leavitt 45, Cape Elizabeth 7 |
| 9.15.2023 – Leavitt 63, York 13 |
| 9.23.2023 – Leavitt 21, Oxford Hills 14 |
| 9.29.2023 – Leavitt 62, Lawrence 32 |
| 10.06.2023 – Leavitt 51, Lewiston 13 |
| 10.14.2023 – Leavitt 35, Thornton Academy 21 |
| 10.20.2023 – Leavitt 34, Cheverus 14 |
| 11.04.2023 – Leavitt 59, Cape Elizabeth 26 |
TBA 11.11.2023 – Fryeburg Academy at Leavitt |
| 11.11.2023 – Leavitt 36, Fryeburg Academy 32 |
11 am 11.18.2023 – Oceanside at Leavitt |
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