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| All Schools |
| All Sports |
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| Field Hockey | | 9.07.2021 – Oxford Hills 4, Messalonskee 0 |
| 9.09.2021 – Messalonskee 4, Camden Hills 0 |
| 9.11.2021 – Messalonskee 4, Mount Blue 1 |
| 9.13.2021 – Messalonskee 3, Brewer 2 |
| 9.14.2021 – Messalonskee 2, Hampden Academy 1 |
| 9.16.2021 – Messalonskee 1, Brunswick 0 |
| 9.18.2021 – Lewiston 2, Messalonskee 1 |
| 9.21.2021 – Messalonskee 2, Edward Little 0 |
| 9.23.2021 – Skowhegan 2, Messalonskee 0 |
| 9.27.2021 – Mount Ararat 2, Messalonskee 0 |
| 9.30.2021 – Mount Blue 1, Messalonskee 1 |
| 10.02.2021 – Messalonskee 2, Winslow 0 |
| 10.13.2021 – Skowhegan 4, Messalonskee 1 |
| 10.23.2021 – Messalonskee 2, Edward Little 0 |
| 10.26.2021 – Messalonskee 2, Lewiston 1 |
| 10.29.2021 – Skowhegan 4, Messalonskee 1 |
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