| Ari Arzumanian (Jr.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 5 | 00:17.31 |
| Max Lindenmayer (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 12 | 00:18.00 |
| Gabriel Tienstra (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 24 | 00:18.35 |
| Abraham Blaesing (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 34 | 00:19.12 |
| Jacob Cipowski (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 47 | 00:20.03 |
| Charles Iverson (So.) | Crown Point Invite (High School) | 2019 Crown Point Boys Cross Country Meet | 56 | 00:20.28 |
| Max Lindenmayer (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 4 | 17:00.80 |
| Ari Arzumanian (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 7 | 17:14.50 |
| Gabriel Tienstra (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 14 | 17:46.80 |
| Juan Angel Olivencia (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 15 | 17:58.00 |
| Charles Iverson (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 28 | 19:29.40 |
