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| All Schools |
| All Sports |
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| Basketball - Boys | | 12.10.2022 – Boothbay Region 66, Madison 48 |
| 12.13.2022 – Madison 79, Telstar 38 |
| 12.20.2022 – Carrabec 73, Madison 61 |
| 12.22.2022 – Hall-Dale 56, Madison 55 |
| 12.28.2022 – Spruce Mountain 58, Madison 30 |
| 1.07.2023 – Dirigo 79, Madison 51 |
| 1.09.2023 – Madison 55, Monmouth Academy 48 |
| 1.11.2023 – Madison 65, Mountain Valley 58 |
| 1.14.2023 – Madison 85, Buckfield 41 |
| 1.21.2023 – Madison 77, Valley 52 |
| 1.24.2023 – Madison 75, Wiscasset 30 |
| 1.27.2023 – Madison 52, Winthrop 51 |
| 1.28.2023 – Mount Abram 79, Madison 52 |
| 1.31.2023 – Lisbon 51, Madison 37 |
| 2.02.2023 – Madison 67, Oak Hill 44 |
| 2.06.2023 – Madison 77, Forest Hills 63 |
| 2.07.2023 – Madison 57, Oak Hill 32 |
| 2.08.2023 – Madison 66, Telstar 24 |
| 2.15.2023 – Madison 52, Waynflete 34 |
| 2.20.2023 – Dirigo 66, Madison 46 |
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