| James Chatman (Sr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 11 | 18:57.18 |
| Aaron Coffer (Sr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 22 | 19:59.57 |
| Amyron Harvey (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 25 | 20:12.50 |
| Elton Amos (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 33 | 20:26.53 |
| Sebastian Watson (Sr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 35 | 20:43.84 |
| Xavier Croom (Jr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 39 | 21:04.18 |
| Chase Hawver (Jr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 63 | 22:40.31 |
| Quentin Espinosa (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 67 | 23:55.10 |
| Daniel Rogers (So.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 73 | 24:55.22 |
| Ian Young (Fr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 75 | 25:44.27 |
| Joseph Bryant (Fr.) | Winchester Cross Country Invitational Boys Meet | Winchester Cross Country Invitational Boys Meet | 80 | 28:06.06 |
