| Cole Benegas (Jr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 3 | 17:34.90 |
| Michael Schwebach (Sr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 7 | 17:43.00 |
| Michael Schwebach (Sr.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 7 | 17:58.90 |
| Logan Hicks (So.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 14 | 18:12.30 |
| Bradyn Hatton (Fr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 18 | 18:29.50 |
| Logan Hicks (So.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 10 | 18:34.70 |
| Cole Benegas (Jr.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 11 | 18:36.50 |
| Zen Ivey (Jr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 20 | 18:39.90 |
| Nico DiMeglio (Sr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 22 | 18:50.00 |
| Parker Fleming (Sr.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 16 | 19:14.30 |
| Bradyn Hatton (Fr.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 18 | 19:22.60 |
| Tyler Allison (Fr.) | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 2021 IHSAA South Dearborn Sectional Boys Cross Country Meet | 33 | 19:34.40 |
| Tyler Allison (Fr.) | East Central Invitational Boys Cross Country Meet | East Central Invitational Boys Cross Country Meet | 19 | 19:39.00 |
