| George Peterson (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 24 | 18:57.00 |
| Aiden Bevan (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 29 | 19:33.40 |
| Sean Stringfellow (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 30 | 19:36.90 |
| Matthew Hutcherson (Fr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 46 | 20:47.40 |
| Evan Johnson (Fr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 51 | 21:43.40 |
| Santiago Palmerin (Sr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 54 | 21:57.00 |
| Eric Johnson (Sr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 55 | 22:28.30 |
