| Wyatt Beck (Sr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 3 | 17:05.60 |
| Brandon Rice (Sr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 5 | 17:23.76 |
| Chance Craig (Sr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 7 | 17:33.36 |
| Jackson Marshall (Jr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 10 | 18:05.20 |
| Carlos Mata (Fr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 18 | 18:28.06 |
| Brayten Furnish (So.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 20 | 18:37.97 |
| Jaxon Konkler (So.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 73 | 20:44.39 |
| Braden Peacock (Jr.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 78 | 20:53.28 |
| Devin Nease (So.) | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 2021 Jeremy Wright Boys Southwestern ( Shelbyville ) Small School Invitational | 159 | 23:29.01 |
