| All Schools |
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| Field Hockey |
| 9.06.2019 – Boothbay Region 4, Hall-Dale 0 |
| 9.11.2019 – Mountain Valley 5, Boothbay Region 3 |
| 9.13.2019 – Spruce Mountain 5, Boothbay Region 2 |
| 9.16.2019 – Winthrop/Monmouth 2, Boothbay Region 0 |
| 9.20.2019 – Boothbay Region 4, Lisbon 0 |
| 9.23.2019 – Oak Hill 5, Boothbay Region 1 |
| 9.25.2019 – Boothbay Region 5, Telstar 0 |
| 9.27.2019 – Boothbay Region 7, Hall-Dale 1 |
| 10.04.2019 – Winthrop/Monmouth 4, Boothbay Region 1 |
| 10.09.2019 – Spruce Mountain 7, Boothbay Region 3 |
04:00 PM 10.16.2019 – Dirigo at Boothbay Region |
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| Football |
| 9.06.2019 – Maranacook 14, Boothbay Region 6 |
| 9.13.2019 – Boothbay Region 46, Old Orchard Beach 30 |
| 9.20.2019 – Boothbay Region 52, Traip Academy 14 |
| 9.28.2019 – Telstar 30, Boothbay Region 18 |
| 10.04.2019 – Boothbay Region 36, Sacopee Valley 0 |
| 10.11.2019 – Yarmouth 50, Boothbay Region 20 |
01:30 PM 10.19.2019 – Boothbay Region at Traip Academy |
07:00 PM 10.25.2019 – Boothbay Region at Old Orchard Beach |
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| Soccer - Girls |
| 9.05.2019 – Dirigo 2, Boothbay Region 1 |
| 9.10.2019 – Buckfield 11, Boothbay Region 0 |
| 9.14.2019 – Mountain Valley 1, Boothbay Region 0 |
| 9.27.2019 – Hall-Dale 1, Boothbay Region 0 |
| 10.02.2019 – Lisbon 1, Boothbay Region 0 |
| 10.04.2019 – Monmouth Academy 1, Boothbay Region 0 |
03:30 PM 10.16.2019 – Winthrop at Boothbay Region |
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