| Jonathan Baxter (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 2 | 16:49.80 |
| Jacob Catizone (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 23 | 18:51.20 |
| Justin Perez (Jr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 32 | 19:47.70 |
| Nathan Pinkerton (Fr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 42 | 20:40.30 |
| Hayden O'Brien (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 43 | 20:40.70 |
| David Bacon (So.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 52 | 21:43.80 |
| Maxwell Archambault (Fr.) | 2019 IHSAA Highland Sectional Boys Cross Country Meet | 2019 IHSAA Highland Boys Cross Country Meet | 56 | 23:11.40 |
