| Riley Smith (Fr.) | North Knox Invitational | | 1 | 18:06.00 |
| Riley Smith (Fr.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 30 | 18:32.00 |
| Riley Smith (Fr.) | WIC Meet | | 25 | 19:04.00 |
| Riley Smith (Fr.) | Terre Haute North Invite | 1A-3A | 42 | 19:17.90 |
| Riley Smith (Fr.) | Terre Haute South Vigo (Terre Haute, IN) | | 14 | 19:30.00 |
| Riley Smith (Fr.) | Riverton Parke Invitational | Riverton Parke Invitational | 20 | 19:38.00 |
| Riley Smith (Fr.) | Shakamak Invitational | | 34 | 19:42.00 |
| Riley Smith (Fr.) | Washington Invitational | | 17 | 19:47.00 |
| Riley Smith (Fr.) | White River Valley | | 7 | 19:51.00 |
| Ben Pirtle (So.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 49 | 20:12.00 |
| Lane Clements (Sr.) | North Knox Invitational | | 6 | 20:21.00 |
| Lane Clements (Sr.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 54 | 20:23.00 |
| Riley Smith (Fr.) | North Central (Farmersburg, IN) | | 1 | 20:26.00 |
| Ben Pirtle (So.) | Terre Haute North Invite | 1A-3A | 79 | 20:37.60 |
| Ben Pirtle (So.) | Shakamak Invitational | | 42 | 20:43.00 |
| Lane Clements (Sr.) | Shakamak Invitational | | 43 | 20:45.00 |
| Riley Smith (Fr.) | Sullivan/North Central/Clay City | | 3 | 20:47.00 |
| Lane Clements (Sr.) | Washington Invitational | | 31 | 20:51.00 |
| Ben Pirtle (So.) | WIC Meet | | 60 | 20:52.00 |
| Lane Clements (Sr.) | WIC Meet | | 63 | 20:58.00 |
| Will Atkinson (Jr.) | North Knox Invitational | | 8 | 21:00.00 |
| Ben Pirtle (So.) | North Central (Farmersburg, IN) | | 2 | 21:00.00 |
| Ben Pirtle (So.) | Terre Haute South Vigo (Terre Haute, IN) | | 26 | 21:06.00 |
| Riley Smith (Fr.) | West Vigo (West Terre Haute, IN) | | 4 | 21:07.00 |
| Lane Clements (Sr.) | Terre Haute South Vigo (Terre Haute, IN) | | 27 | 21:12.00 |
| Riley Smith (Fr.) | Chad Smith Scholarship Invitational | | 12 | 21:17.10 |
| Lane Clements (Sr.) | North Central (Farmersburg, IN) | | 3 | 21:18.00 |
| Lane Clements (Sr.) | White River Valley | | 12 | 21:19.00 |
| Will Atkinson (Jr.) | Terre Haute North Invite | 1A-3A | 97 | 21:21.50 |
| Lane Clements (Sr.) | Terre Haute North Invite | 1A-3A | 103 | 21:34.30 |
| Ben Pirtle (So.) | Sullivan/North Central/Clay City | | 4 | 21:35.00 |
| Ben Pirtle (So.) | Chad Smith Scholarship Invitational | | 17 | 21:37.50 |
| Ben Pirtle (So.) | Riverton Parke Invitational | Riverton Parke Invitational | 47 | 21:40.00 |
| Ben Pirtle (So.) | Washington Invitational | | 36 | 21:46.00 |
| Ben Pirtle (So.) | West Vigo (West Terre Haute, IN) | | 8 | 21:56.00 |
| Will Atkinson (Jr.) | Shakamak Invitational | | 51 | 22:01.00 |
| Will Atkinson (Jr.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 71 | 22:01.00 |
| Lane Clements (Sr.) | Sullivan/North Central/Clay City | | 9 | 22:12.00 |
| Lane Clements (Sr.) | Riverton Parke Invitational | Riverton Parke Invitational | 56 | 22:20.00 |
| Will Atkinson (Jr.) | Riverton Parke Invitational | Riverton Parke Invitational | 57 | 22:21.00 |
| Will Atkinson (Jr.) | North Central (Farmersburg, IN) | | 4 | 22:32.00 |
| Will Atkinson (Jr.) | White River Valley | | 17 | 22:41.00 |
| Will Atkinson (Jr.) | WIC Meet | | 80 | 22:51.00 |
| Will Atkinson (Jr.) | Washington Invitational | | 42 | 22:52.00 |
| Will Atkinson (Jr.) | Terre Haute South Vigo (Terre Haute, IN) | | 28 | 23:08.00 |
| Lane Clements (Sr.) | Chad Smith Scholarship Invitational | | 33 | 23:30.20 |
| Dalton Land (So.) | Terre Haute North Invite | 1A-3A | 134 | 23:41.30 |
| Dalton Land (So.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 80 | 23:47.00 |
| Dalton Land (So.) | North Central (Farmersburg, IN) | | 6 | 23:51.00 |
| Dalton Land (So.) | WIC Meet | | 87 | 24:06.00 |
| Lane Clements (Sr.) | West Vigo (West Terre Haute, IN) | | 12 | 24:18.00 |
| Alex Arthur (Fr.) | North Knox Invitational | | 15 | 24:42.00 |
| Will Atkinson (Jr.) | Chad Smith Scholarship Invitational | | 38 | 24:46.20 |
| Will Atkinson (Jr.) | Sullivan/North Central/Clay City | | 16 | 24:51.00 |
| Nick Hornback (Fr.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 82 | 24:54.00 |
| Dalton Land (So.) | Shakamak Invitational | | 61 | 25:07.00 |
| Nick Hornback (Fr.) | North Knox Invitational | | 16 | 25:15.00 |
| Dalton Land (So.) | Terre Haute South Vigo (Terre Haute, IN) | | 29 | 25:43.00 |
| Will Atkinson (Jr.) | West Vigo (West Terre Haute, IN) | | 13 | 25:46.00 |
| Dalton Land (So.) | Washington Invitational | | 48 | 25:49.00 |
| Nick Hornback (Fr.) | Riverton Parke Invitational | Riverton Parke Invitational | 77 | 25:55.00 |
| Nick Hornback (Fr.) | North Central (Farmersburg, IN) | | 9 | 26:00.00 |
| Alex Arthur (Fr.) | Terre Haute North Invite | 1A-3A | 158 | 26:33.30 |
| Alex Arthur (Fr.) | White River Valley | | 25 | 26:55.00 |
| Nick Hornback (Fr.) | Chad Smith Scholarship Invitational | | 50 | 27:09.20 |
| Alex Arthur (Fr.) | Shakamak Invitational | | 64 | 27:26.00 |
| Alex Arthur (Fr.) | Washington Invitational | | 49 | 27:31.00 |
| Dalton Land (So.) | Sullivan/North Central/Clay City | | 22 | 27:47.00 |
| Alex Arthur (Fr.) | Bloomfield Invitational | | 32 | 28:00.00 |
| Alex Arthur (Fr.) | Riverton Parke Invitational | Riverton Parke Invitational | 87 | 28:24.00 |
| Dalton Land (So.) | West Vigo (West Terre Haute, IN) | | | 28:54.00 |
| Alex Arthur (Fr.) | WIC Meet | | 95 | 28:54.00 |
| Alex Arthur (Fr.) | Terre Haute South Vigo (Terre Haute, IN) | | 32 | 29:04.00 |
| Alex Arthur (Fr.) | Sullivan/North Central/Clay City | | 25 | 29:07.00 |
| Alex Arthur (Fr.) | North Central (Farmersburg, IN) | | 12 | 29:11.00 |
| Alex Arthur (Fr.) | Chad Smith Scholarship Invitational | | 55 | 29:16.80 |
| Nick Hornback (Fr.) | West Vigo (West Terre Haute, IN) | | 18 | 30:31.00 |
| Tanner Hancock (Jr.) | North Knox Invitational | | 18 | 31:24.00 |
| Tanner Hancock (Jr.) | Terre Haute North Invite | 1A-3A | 165 | 31:59.40 |
| Tanner Hancock (Jr.) | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 2016 IHSAA Terre Haute North Sectional Boys Cross Country Meet | 86 | 32:09.00 |
| Tanner Hancock (Jr.) | Shakamak Invitational | | 67 | 32:48.00 |
| Tanner Hancock (Jr.) | Chad Smith Scholarship Invitational | | 62 | 34:06.30 |
| Tanner Hancock (Jr.) | Washington Invitational | | 53 | 34:17.00 |
| Tanner Hancock (Jr.) | WIC Meet | | 96 | 34:50.00 |
| Tanner Hancock (Jr.) | Riverton Parke Invitational | Riverton Parke Invitational | 92 | 35:00.00 |
| Tanner Hancock (Jr.) | Terre Haute South Vigo (Terre Haute, IN) | | 33 | 36:03.00 |
| Tanner Hancock (Jr.) | White River Valley | | 28 | 36:20.00 |
| Tanner Hancock (Jr.) | North Central (Farmersburg, IN) | | 13 | 37:33.00 |
| Alex Arthur (Fr.) | West Vigo (West Terre Haute, IN) | | 19 | 41:22.00 |
| Tanner Hancock (Jr.) | West Vigo (West Terre Haute, IN) | | 20 | 41:37.00 |
