| All Schools |
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| Field Hockey |
| 9.05.2019 – Messalonskee 3, Mount Ararat 1 |
| 9.10.2019 – Mount Blue 5, Messalonskee 1 |
| 9.12.2019 – Messalonskee 3, Oxford Hills 2 |
| 9.17.2019 – Skowhegan 5, Messalonskee 2 |
| 9.19.2019 – Messalonskee 3, Cony 2 |
| 9.21.2019 – Brunswick 4, Messalonskee 3 |
| 9.26.2019 – Mount Blue 4, Messalonskee 0 |
| 10.01.2019 – Messalonskee 5, Camden Hills 1 |
| 10.03.2019 – Messalonskee 2, Bangor 1 |
| 10.07.2019 – Messalonskee 4, Edward Little 1 |
| 10.08.2019 – Messalonskee 6, Lewiston 3 |
| 10.10.2019 – Messalonskee 4, Brewer 1 |
03:00 PM 10.14.2019 – Messalonskee at Skowhegan |
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| Football |
| 9.06.2019 – Falmouth/Greely 52, Messalonskee 6 |
| 9.13.2019 – Mount Blue 43, Messalonskee 16 |
| 9.20.2019 – Cony 28, Messalonskee 0 |
| 9.27.2019 – Hampden Academy 30, Messalonskee 16 |
| 10.04.2019 – Lawrence 54, Messalonskee 22 |
| 10.11.2019 – Skowhegan 38, Messalonskee 8 |
07:00 PM 10.18.2019 – Gardiner at Messalonskee |
07:00 PM 10.25.2019 – Brunswick at Messalonskee |
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| Soccer - Boys |
| 9.05.2019 – Messalonskee 4, Brewer 3 |
| 9.10.2019 – Messalonskee 2, Bangor 1 |
| 9.14.2019 – Camden Hills 4, Messalonskee 0 |
| 9.19.2019 – Lewiston 7, Messalonskee 1 |
| 9.21.2019 – Messalonskee 1, Winslow 1 |
| 9.25.2019 – Messalonskee 2, Oxford Hills 1 |
| 9.28.2019 – Messalonskee 2, Skowhegan 1 |
| 10.01.2019 – Brunswick 6, Messalonskee 0 |
| 10.03.2019 – Cony 0, Messalonskee 0 |
| 10.08.2019 – Hampden Academy 3, Messalonskee 1 |
| 10.11.2019 – Mount Ararat 1, Messalonskee 0 |
06:30 PM 10.15.2019 – Mount Blue at Messalonskee |
06:30 PM 10.17.2019 – Edward Little at Messalonskee |
03:30 PM 10.22.2019 – Messalonskee at Cony |
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| Soccer - Girls |
| 9.05.2019 – Messalonskee 4, Brewer 1 |
| 9.10.2019 – Messalonskee 3, Bangor 2 |
| 9.14.2019 – Camden Hills 6, Messalonskee 1 |
| 9.19.2019 – Lewiston 1, Messalonskee 1 |
| 9.21.2019 – Winslow 1, Messalonskee 1 |
| 9.24.2019 – Oxford Hills 5, Messalonskee 1 |
| 9.27.2019 – Messalonskee 5, Skowhegan 0 |
| 10.08.2019 – Messalonskee 2, Hampden Academy 2 |
| 10.11.2019 – Mount Ararat 2, Messalonskee 0 |
06:00 PM 10.15.2019 – Messalonskee at Mount Blue |
03:30 PM 10.18.2019 – Messalonskee at Edward Little |
06:30 PM 10.22.2019 – Cony at Messalonskee |
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