| All Schools |
| |
| Field Hockey |
| 9.09.2019 – Dirigo 1, Lisbon 0 |
| 9.11.2019 – Dirigo 4, Oak Hill 1 |
| 9.13.2019 – Dirigo 5, Telstar 3 |
| 9.16.2019 – Dirigo 2, Hall-Dale 1 |
| 9.20.2019 – Dirigo 3, Mountain Valley 2 |
| 9.23.2019 – Dirigo 3, Spruce Mountain 2 |
| 9.25.2019 – Winthrop/Monmouth 3, Dirigo 2 |
| 9.30.2019 – Dirigo 4, Lisbon 0 |
| 10.02.2019 – Oak Hill 4, Dirigo 3 |
| 10.04.2019 – Spruce Mountain 3, Dirigo 1 |
| 10.09.2019 – Dirigo 6, Telstar 0 |
04:00 PM 10.16.2019 – Dirigo at Boothbay Region |
| |
| Football |
| 9.06.2019 – Lake Region 34, Dirigo 13 |
| 9.13.2019 – Spruce Mountain 1, Dirigo 0 |
| 9.20.2019 – Carrabec/Madison Co-op 1, Dirigo 0 |
| 9.27.2019 – Oak Hill 2, Dirigo 0 |
| 10.11.2019 – Freeport 2, Dirigo 0 |
07:00 PM 10.18.2019 – Mountain Valley at Dirigo |
| |
| Soccer - Boys |
| 9.11.2019 – Dirigo 3, Buckfield 2 |
| 9.16.2019 – Lisbon 7, Dirigo 1 |
| 9.18.2019 – Dirigo 2, Mountain Valley 1 |
| 9.20.2019 – Oak Hill 5, Dirigo 0 |
| 10.03.2019 – Hall-Dale 4, Dirigo 0 |
03:30 PM 10.15.2019 – Dirigo at Telstar |
03:30 PM 10.17.2019 – Lisbon at Dirigo |
| |
| Soccer - Girls |
| 9.05.2019 – Dirigo 2, Boothbay Region 1 |
| 9.12.2019 – Buckfield 7, Dirigo 0 |
| 9.14.2019 – Madison 6, Dirigo 0 |
| 9.17.2019 – Mountain Valley 6, Dirigo 0 |
| 9.19.2019 – Oak Hill 11, Dirigo 0 |
| 9.23.2019 – Telstar 7, Dirigo 0 |
| 9.25.2019 – Wiscasset 6, Dirigo 0 |
| 10.02.2019 – Hall-Dale 4, Dirigo 0 |
| 10.08.2019 – Monmouth Academy 8, Dirigo 0 |
03:30 PM 10.16.2019 – Spruce Mountain at Dirigo |
03:30 PM 10.18.2019 – Dirigo at Winthrop |
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