| Date | Opponent | Result |
|---|---|---|
| Thursday, October 16, 2025 |
|---|
| Union City 3 at Middleton 2 |
| Tuesday, August 26, 2025 |
| Collinwood 3 at Middleton 1 |
| Friday, August 22, 2025 |
| Jackson South Side 1 at Middleton 3 |
| Thursday, August 21, 2025 |
| Middleton 3 at Bolivar Central 0 |
| Madison Academic Magnet | 5-0 | 15-10 |
| Trinity Christian | 2-1 | 7-8 |
| Scotts Hill | 2-6 | 5-15-1 |
| Decatur County Riverside | 1-1 | 1-1-1 |
| Middleton | 0-2 | 0-8 |