| Jackson Miller (Sr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 4 | 00:16.06 |
| Jackson Miller (Sr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 1 | 00:16.31 |
| Drew O'Neil (Sr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 35 | 00:16.53 |
| Abram Eckman (So.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 3 | 00:16.55 |
| Abram Eckman (So.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 36 | 00:16.57 |
| Drew O'Neil (Sr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 4 | 00:17.06 |
| Jaryn Weinel (Fr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 45 | 00:17.07 |
| William Gubbins (Fr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 53 | 00:17.18 |
| Jaryn Weinel (Fr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 9 | 00:17.42 |
| Cameron Eckstein (Sr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 80 | 00:17.51 |
| William Gubbins (Fr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 11 | 00:17.55 |
| Harrison Hulsman (Fr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 86 | 00:17.58 |
| Cameron Eckstein (Sr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 13 | 00:18.11 |
| Harrison Hulsman (Fr.) | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 2019 IHSAA Jasper Sectional Boys Cross Country Meet | 17 | 00:18.36 |
