| All Schools |
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| Baseball |
| 5.03.2021 – Gardiner 11, Winthrop 1 |
| 5.07.2021 – Monmouth Academy 2, Winthrop 1 |
| 5.10.2021 – Maranacook 4, Winthrop 3 |
| 5.11.2021 – Mount Abram 10, Winthrop 5 |
| 5.17.2021 – Winthrop 12, Carrabec 1 |
| 6.08.2021 – Maranacook 4, Winthrop 1 |
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| Basketball - Boys |
| 1.19.2021 – Cony 57, Winthrop 46 |
| 1.21.2021 – Boothbay Region 56, Winthrop 41 |
| 2.04.2021 – Winthrop 44, Boothbay Region 35 |
| 2.09.2021 – Maranacook 81, Winthrop 42 |
| 2.10.2021 – Winthrop 48, Madison 45 |
| 2.23.2021 – Winthrop 56, Spruce Mountain 42 |
| 2.25.2021 – Winthrop 71, Richmond 35 |
| 3.10.2021 – Winthrop 41, Spruce Mountain 38 |
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| Basketball - Girls |
| 1.21.2021 – Winthrop 55, Boothbay Region 37 |
| 2.01.2021 – Gardiner 56, Winthrop 45 |
| 2.04.2021 – Winthrop 44, Boothbay Region 26 |
| 2.09.2021 – Maranacook 48, Winthrop 40 |
| 2.23.2021 – Winthrop 31, Spruce Mountain 24 |
| 2.25.2021 – Winthrop 71, Richmond 35 |
| 3.09.2021 – Carrabec 44, Winthrop 43 |
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| Field Hockey |
| 10.21.2020 – Winthrop 3, Oak Hill 2 |
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| Softball |
| 5.10.2021 – Maranacook 9, Winthrop 1 |
| 5.24.2021 – Buckfield 4, Winthrop 3 |
| 5.26.2021 – Winthrop 9, Saint Dominic 7 |
| 6.08.2021 – Winthrop 6, Lisbon 2 |
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