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| • Games for All Schools in September, 2023 |
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| Football |
| 9.1.2023 – Poland Regional 46, Madison 0 |
| 9.9.2023 – Winslow 16, Madison 14 |
| 9.15.2023 – Maine Central Institute 28, Madison 12 |
| 9.22.2023 – Foxcroft Academy 68, Madison 0 |
| 9.29.2023 – Belfast 35, Madison 0 |
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| Soccer - Girls |
| 9.5.2023 – Madison 14, Wiscasset 0 |
| 9.7.2023 – Madison 10, Dirigo 0 |
| 9.9.2023 – Madison 9, Searsport 0 |
| 9.13.2023 – Madison 6, Carrabec 2 |
| 9.19.2023 – Richmond 5, Madison 4 |
| 9.21.2023 – Madison 7, Valley 0 |
| 9.28.2023 – Madison 6, Carrabec 0 |
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