| Johah Cornett (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 10 | 18:51.18 |
| Tate Chasteen (Jr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 12 | 19:10.11 |
| Mattias Hermlin (Fr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 13 | 19:12.88 |
| Grayson Hawkins (Jr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 16 | 19:24.26 |
| Clay Johnson (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 19 | 19:37.57 |
| Jayden Cornett (Sr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 21 | 19:43.35 |
| Mason Flynn (Fr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 40 | 21:05.42 |
| Conner Scheer (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 46 | 21:29.16 |
| Joshua Eliason (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 74 | 25:26.56 |
