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| All Schools |
| All Sports |
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| Soccer - Girls | | 9.01.2023 – Hall-Dale 1, Winthrop/Monmouth 0 |
| 9.05.2023 – Winthrop/Monmouth 7, Spruce Mountain 1 |
| 9.09.2023 – Winthrop/Monmouth 10, Cony 0 |
| 9.12.2023 – Maranacook 3, Winthrop/Monmouth 1 |
| 9.15.2023 – Winthrop/Monmouth 6, Oak Hill 0 |
| 9.18.2023 – Winthrop/Monmouth 5, Mountain Valley 0 |
| 9.20.2023 – Winthrop/Monmouth 3, Mount Abram 0 |
| 9.23.2023 – Winthrop/Monmouth 5, Oak Hill 0 |
| 9.25.2023 – Winthrop/Monmouth 5, Mountain Valley 0 |
| 9.27.2023 – Winthrop/Monmouth 7, Spruce Mountain 1 |
| 10.04.2023 – Winthrop/Monmouth 2, Mountain Valley 0 |
| 10.06.2023 – Leavitt 1, Winthrop/Monmouth 1 |
| 10.11.2023 – Maranacook 3, Winthrop/Monmouth 0 |
| 10.14.2023 – North Yarmouth Academy 5, Winthrop/Monmouth 0 |
| 10.16.2023 – Hall-Dale 4, Winthrop/Monmouth 0 |
| 10.24.2023 – Hall-Dale 2, Winthrop/Monmouth 1 |
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