| All Schools |
| |
| Basketball - Boys |
| 12.07.2019 – Winthrop 83, Carrabec 44 |
| 12.12.2019 – Winthrop 66, Madison 41 |
| 12.18.2019 – Winthrop 65, Mountain Valley 34 |
| 12.20.2019 – Winthrop 65, Oak Hill 54 |
| 12.23.2019 – Winthrop 62, Telstar 39 |
| 12.27.2019 – Winthrop 84, Hall-Dale 39 |
| 1.03.2020 – Winthrop 59, Monmouth Academy 46 |
| 1.06.2020 – Winthrop 75, Wiscasset 20 |
| 1.07.2020 – Winthrop 54, Lisbon 45 |
| 1.09.2020 – Winthrop 66, Mount Abram 65 |
| 1.13.2020 – Winthrop 57, Dirigo 50 |
| 1.15.2020 – Spruce Mountain 52, Winthrop 41 |
| 1.21.2020 – Winthrop 75, Boothbay Region 69 |
| 1.23.2020 – Winthrop 49, Mountain Valley 31 |
| 1.27.2020 – Winthrop 72, Lisbon 40 |
06:30 PM 1.31.2020 – Spruce Mountain at Winthrop |
06:30 PM 2.05.2020 – Oak Hill at Winthrop |
| |
| Basketball - Girls |
| 12.09.2019 – Winthrop 60, Lisbon 17 |
| 12.11.2019 – Winthrop 60, Monmouth Academy 53 |
| 12.13.2019 – Winthrop 46, Mountain Valley 24 |
| 12.19.2019 – Winthrop 64, Spruce Mountain 28 |
| 12.27.2019 – Winthrop 73, Hall-Dale 21 |
| 1.04.2020 – Winthrop 52, Dirigo 32 |
| 1.06.2020 – Winthrop 62, Wiscasset 8 |
| 1.08.2020 – Boothbay Region 51, Winthrop 49 |
| 1.10.2020 – Winthrop 62, Oak Hill 60 |
| 1.14.2020 – Winthrop 77, Mount Abram 16 |
| 1.22.2020 – Winthrop 65, Mountain Valley 55 |
| 1.24.2020 – Boothbay Region 55, Winthrop 51 |
06:30 PM 1.30.2020 – Hall-Dale at Winthrop |
06:30 PM 2.04.2020 – Winthrop at Monmouth Academy |
05:00 PM 2.05.2020 – Oak Hill at Winthrop |
| |
| Soccer - Girls |
| 9.05.2019 – Winthrop 2, Buckfield 1 |
| 9.10.2019 – Winthrop 5, Madison 2 |
| 9.12.2019 – Winthrop 7, Mountain Valley 1 |
| 9.17.2019 – Winthrop 4, Telstar 4 |
| 9.19.2019 – Winthrop 5, Wiscasset 0 |
| 9.23.2019 – Winthrop 4, Carrabec 1 |
| 9.25.2019 – Hall-Dale 5, Winthrop 4 |
| 9.27.2019 – Lisbon 2, Winthrop 1 |
| 10.02.2019 – Monmouth Academy 2, Winthrop 0 |
| 10.08.2019 – Winthrop 5, Spruce Mountain 1 |
| 10.18.2019 – Winthrop 5, Dirigo 0 |
| 10.25.2019 – Carrabec 2, Winthrop 0 |
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