| Riley Reeder (Sr.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 19 | 00:18.27 |
| La'Javon Thompson (Jr.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 29 | 00:18.59 |
| Omar Taylor (Sr.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 76 | 00:21.35 |
| Seth Hunt (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 84 | 00:22.08 |
| Riley Reeder (Sr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 11 | 17:40.90 |
| La'Javon Thompson (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 17 | 18:03.50 |
| Omar Taylor (Sr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 25 | 19:08.20 |
| Noah Frazier (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 37 | 20:09.00 |
| Jordan Steele (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 38 | 20:16.50 |
