| Joey Copeland (Jr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 3 | 00:16.57 |
| Billy Duszynski (Jr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 5 | 00:17.06 |
| Mitch Polaski (Jr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 6 | 00:17.06 |
| Isaac Beatty (So.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 9 | 00:17.30 |
| Matt Blair (Sr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 22 | 00:18.02 |
| Josh Chen (Fr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 24 | 00:18.04 |
| Aaron Balka (Sr.) | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 2016 IHSAA Crown Point Regional Boys Cross Country Meet | 46 | 00:19.01 |
| Joey Copeland (Jr.) | Harrison Invitational | Harrison Boys Invitational | 3 | 16:02.50 |
| Isaac Beatty (So.) | Harrison Invitational | Harrison Boys Invitational | 11 | 16:22.20 |
| Mitch Polaski (Jr.) | Harrison Invitational | Harrison Boys Invitational | 17 | 16:31.30 |
| Aaron Balka (Sr.) | Harrison Invitational | Harrison Boys Invitational | 56 | 17:23.20 |
| Carter Goldman (So.) | Harrison Invitational | Harrison Boys Invitational | 76 | 17:41.90 |
| Jack Tinsley (So.) | Harrison Invitational | Harrison Boys Invitational | 88 | 17:56.40 |
