| All Schools |
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| Field Hockey |
| 9.04.2019 – Dexter 3, Piscataquis 0 |
| 9.06.2019 – Dexter 3, Orono 0 |
| 9.10.2019 – Dexter 7, Central 0 |
| 9.12.2019 – Foxcroft Academy 4, Dexter 0 |
| 9.16.2019 – Dexter 4, Mattanawcook/Penobscot 0 |
| 9.18.2019 – Dexter 2, Orono 0 |
| 9.20.2019 – Dexter 2, Schenck/Stearns 0 |
| 9.26.2019 – Dexter 6, Mattanawcook/Penobscot 0 |
| 9.28.2019 – Foxcroft Academy 3, Dexter 1 |
| 10.05.2019 – Dexter 5, Central 0 |
| 10.10.2019 – Old Town 1, Dexter 0 |
04:00 PM 10.14.2019 – Schenck/Stearns at Dexter |
04:00 PM 10.16.2019 – Dexter at Old Town |
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| Football |
| 9.07.2019 – Dexter 37, Carrabec/Madison Co-op 10 |
| 9.13.2019 – Bucksport 43, Dexter 7 |
| 9.20.2019 – Dexter 28, Houlton/Hodgdon/GHCA 7 |
| 10.05.2019 – Dexter 61, Washington Academy 16 |
| 10.12.2019 – Dexter 27, Foxcroft Academy 21 |
01:00 PM 10.19.2019 – Mount View at Dexter |
07:00 PM 10.25.2019 – Dexter at Mattanawcook/Lee/Penobscot |
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| Soccer - Boys |
| 9.07.2019 – Piscataquis 3, Dexter 1 |
| 9.10.2019 – Foxcroft Academy 15, Dexter 2 |
| 9.12.2019 – Bucksport 4, Dexter 1 |
| 9.17.2019 – Orono 12, Dexter 1 |
| 9.19.2019 – Searsport 3, Dexter 2 |
| 9.21.2019 – Central 9, Dexter 2 |
| 9.25.2019 – Foxcroft Academy 8, Dexter 0 |
| 9.28.2019 – Penquis Valley 4, Dexter 1 |
| 10.01.2019 – Piscataquis 9, Dexter 2 |
| 10.03.2019 – Central 11, Dexter 2 |
| 10.05.2019 – Orono 9, Dexter 0 |
04:00 PM 10.16.2019 – Dexter at George Stevens |
04:00 PM 10.22.2019 – Penquis Valley at Dexter |
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| Soccer - Girls |
| 9.06.2019 – Piscataquis 4, Dexter 3 |
| 9.09.2019 – Foxcroft Academy 4, Dexter 1 |
| 9.11.2019 – Bucksport 3, Dexter 2 |
| 9.16.2019 – Orono 1, Dexter 0 |
| 9.18.2019 – Dexter 2, Searsport 0 |
| 9.23.2019 – Central 4, Dexter 1 |
| 9.28.2019 – Dexter 7, Penquis Valley 2 |
| 10.02.2019 – Dexter 3, Piscataquis 0 |
| 10.05.2019 – Dexter 4, Central 3 |
| 10.08.2019 – Orono 3, Dexter 2 |
| 10.10.2019 – Dexter 8, Searsport 2 |
04:00 PM 10.15.2019 – Penquis Valley at Dexter |
04:00 PM 10.17.2019 – Dexter at George Stevens |
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