| Isaiah Sims (Sr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 36 | 19:56.50 |
| Quimari Peterson (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 49 | 21:35.00 |
| Cornelius Brown (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 50 | 21:36.70 |
| Kameron Johnson (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 57 | 23:18.00 |
| Davion Chandler (Fr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 59 | 25:18.30 |
