| All Schools |
| |
| Football |
| 9.01.2023 – Poland Regional 46, Madison 0 |
| 9.09.2023 – 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 |
| 10.06.2023 – John Bapst 48, Madison 8 |
| 10.13.2023 – Old Town 6, Madison 0 |
| 10.20.2023 – Hampden Academy 49, Madison 8 |
| |
| Soccer - Girls |
| 9.05.2023 – Madison 14, Wiscasset 0 |
| 9.07.2023 – Madison 10, Dirigo 0 |
| 9.09.2023 – 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 |
| 10.02.2023 – Madison 9, Dirigo 0 |
| 10.05.2023 – Madison 7, Lisbon 0 |
| 10.07.2023 – Richmond 5, Madison 2 |
| 10.11.2023 – Madison 6, Telstar 1 |
| 10.13.2023 – Madison 8, Valley 0 |
| 10.16.2023 – Madison 4, Telstar 2 |
| 10.24.2023 – Madison 8, Dirigo 0 |
| 10.31.2023 – Madison 8, Carrabec 0 |
| 11.07.2023 – Madison 5, Rangeley 2 |
| 11.11.2023 – Madison 3, Penquis Valley 1 |
