| Benjamin Mckinley (So.) | Washington Invite | | 22 | 19:25.00 |
| Benjamin Mckinley (So.) | North Knox (Bicknell, IN) | | 1 | 19:39.00 |
| Benjamin Mckinley (So.) | Shakamak Invitational | | 30 | 19:56.00 |
| Benjamin Mckinley (So.) | North Central/Linton | | 1 | 20:11.00 |
| Benjamin Mckinley (So.) | 2021 IHSAA Sectional Terre Haute | | 32 | 20:19.00 |
| Benjamin Mckinley (So.) | Tiger Cub Invite | | 12 | 20:20.00 |
| Benjamin Mckinley (So.) | Terre Haute Savings Bank State Preview | | 40 | 20:32.00 |
| Benjamin Mckinley (So.) | Nike Twilight | | 176 | 20:34.00 |
| Benjamin Mckinley (So.) | Western Indiana Conference | | 46 | 20:37.00 |
| Benjamin Mckinley (So.) | Riverton Parke Invitational | | 13 | 20:50.00 |
| Benjamin Mckinley (So.) | Chad Smith Invite | | 14 | 20:57.00 |
| Kaden Helms (Fr.) | North Central/Linton | | 2 | 21:12.00 |
| Jeremy Salesman (Fr.) | Tiger Cub Invite | | 16 | 21:25.00 |
| Jeremy Salesman (Fr.) | Shakamak Invitational | | 40 | 21:28.00 |
| Benjamin Mckinley (So.) | West Vigo (West Terre Haute, IN) | | 4 | 21:28.00 |
| Jeremy Salesman (Fr.) | North Knox (Bicknell, IN) | | 2 | 21:37.00 |
| Jeremy Salesman (Fr.) | Washington Invite | | 35 | 21:38.00 |
| Benjamin Mckinley (So.) | Terre Haute South Valley Boys Cross Country Kick-Off Meet | Terre Haute South Valley Boys Cross Country Kick-Off Meet | 239 | 21:41.00 |
| Kaden Helms (Fr.) | Nike Twilight | | 235 | 21:43.00 |
| Jeremy Salesman (Fr.) | 2021 IHSAA Sectional Terre Haute | | 46 | 21:49.00 |
| Benjamin Mckinley (So.) | Clay City Invite | | 22 | 21:54.00 |
| Kaden Helms (Fr.) | 2021 IHSAA Sectional Terre Haute | | 47 | 22:03.00 |
| Will Brooks (So.) | North Central/Linton | | 3 | 22:10.00 |
| Will Brooks (So.) | Shakamak Invitational | | 45 | 22:15.00 |
| Kaden Helms (Fr.) | Washington Invite | | 39 | 22:16.00 |
| Jeremy Salesman (Fr.) | Terre Haute Savings Bank State Preview | | 64 | 22:25.00 |
| Kaden Helms (Fr.) | Terre Haute South Valley Boys Cross Country Kick-Off Meet | Terre Haute South Valley Boys Cross Country Kick-Off Meet | 253 | 22:28.00 |
| Jeremy Salesman (Fr.) | Western Indiana Conference | | 61 | 22:35.00 |
| Zack Gibbs (Fr.) | North Central/Linton | | 4 | 22:53.00 |
| Zack Gibbs (Fr.) | Shakamak Invitational | | 50 | 22:55.00 |
| Will Brooks (So.) | Washington Invite | | 46 | 22:59.00 |
| Kaden Helms (Fr.) | Shakamak Invitational | | 52 | 23:06.00 |
| Kaden Helms (Fr.) | Tiger Cub Invite | | 26 | 23:07.00 |
| Will Brooks (So.) | Western Indiana Conference | | 63 | 23:08.00 |
| Kaden Helms (Fr.) | Western Indiana Conference | | 64 | 23:11.00 |
| Will Brooks (So.) | 2021 IHSAA Sectional Terre Haute | | 53 | 23:14.00 |
| Jeremy Salesman (Fr.) | North Central/Linton | | 6 | 23:20.00 |
| Will Brooks (So.) | Tiger Cub Invite | | 28 | 23:28.00 |
| Zack Gibbs (Fr.) | Nike Twilight | | 282 | 23:35.00 |
| Zack Gibbs (Fr.) | North Knox (Bicknell, IN) | | 3 | 23:37.00 |
| Will Brooks (So.) | Nike Twilight | | 284 | 23:39.00 |
| Jacob Chastain (So.) | 2021 IHSAA Sectional Terre Haute | | 59 | 23:41.00 |
| Jeremy Salesman (Fr.) | Nike Twilight | | 287 | 23:49.00 |
| Jacob Chastain (So.) | North Knox (Bicknell, IN) | | 4 | 23:56.00 |
| Zack Gibbs (Fr.) | Washington Invite | | 48 | 23:56.00 |
| Kaden Helms (Fr.) | West Vigo (West Terre Haute, IN) | | 6 | 23:59.00 |
| Jacob Chastain (So.) | Shakamak Invitational | | 57 | 24:09.00 |
| Jacob Chastain (So.) | North Central/Linton | | 9 | 24:10.00 |
| Will Brooks (So.) | Riverton Parke Invitational | | 44 | 24:20.00 |
| Will Brooks (So.) | Chad Smith Invite | | 31 | 24:22.00 |
| Will Brooks (So.) | West Vigo (West Terre Haute, IN) | | 7 | 24:35.00 |
| Zack Gibbs (Fr.) | Western Indiana Conference | | 70 | 24:35.00 |
| Will Brooks (So.) | Terre Haute South Valley Boys Cross Country Kick-Off Meet | Terre Haute South Valley Boys Cross Country Kick-Off Meet | 278 | 24:53.00 |
| Jacob Chastain (So.) | Western Indiana Conference | | 71 | 24:56.00 |
| Jacob Chastain (So.) | Washington Invite | | 49 | 24:58.00 |
| Zack Gibbs (Fr.) | 2021 IHSAA Sectional Terre Haute | | 64 | 25:13.00 |
| Zack Gibbs (Fr.) | Tiger Cub Invite | | 33 | 25:21.00 |
| Chad Mccammon (So.) | Washington Invite | | 52 | 25:27.00 |
| Will Brooks (So.) | Clay City Invite | | 48 | 25:28.00 |
| Jacob Chastain (So.) | Nike Twilight | | 299 | 25:28.00 |
| Zack Gibbs (Fr.) | Terre Haute Savings Bank State Preview | | 91 | 25:28.00 |
| Jacob Chastain (So.) | Tiger Cub Invite | | 34 | 25:29.00 |
| Zack Gibbs (Fr.) | Riverton Parke Invitational | | 51 | 25:37.00 |
| Chad Mccammon (So.) | 2021 IHSAA Sectional Terre Haute | | 68 | 25:42.00 |
| Will Brooks (So.) | Terre Haute Savings Bank State Preview | | 92 | 25:44.00 |
| Jacob Chastain (So.) | Riverton Parke Invitational | | 52 | 25:45.00 |
| Chad Mccammon (So.) | Nike Twilight | | 301 | 25:55.00 |
| Chad Mccammon (So.) | Western Indiana Conference | | 74 | 26:14.00 |
| Zack Gibbs (Fr.) | West Vigo (West Terre Haute, IN) | | 9 | 26:18.00 |
| Jacob Chastain (So.) | Terre Haute Savings Bank State Preview | | 95 | 26:19.00 |
| Chad Mccammon (So.) | North Central/Linton | | 12 | 26:25.00 |
| Chad Mccammon (So.) | Shakamak Invitational | | 58 | 26:42.00 |
| Chad Mccammon (So.) | Terre Haute Savings Bank State Preview | | 96 | 26:42.00 |
| Chad Mccammon (So.) | North Knox (Bicknell, IN) | | 6 | 27:19.00 |
| Zack Gibbs (Fr.) | Clay City Invite | | 54 | 27:40.00 |
| Jacob Chastain (So.) | Chad Smith Invite | | 44 | 27:52.00 |
| Jacob Chastain (So.) | Clay City Invite | | 56 | 28:07.00 |
| Jeremy Salesman (Fr.) | Clay City Invite | | 59 | 29:26.00 |
| Chad Mccammon (So.) | Tiger Cub Invite | | 39 | 29:31.00 |
| Chad Mccammon (So.) | Clay City Invite | | 63 | 31:19.00 |
| Kaden Helms (Fr.) | Chad Smith Invite | | 36 | 35:27.00 |
