| Walker Brocksmith (Fr.) | Bloomfield Invite | | 25 | 00:23.00 |
| Alex Baker (Fr.) | North Central (Farmersburg, IN) | | 16 | 00:30.36 |
| Dosson Lamb (So.) | Shakamak Invitational | | 5 | 17:33.00 |
| Preston Anthony (Fr.) | Shakamak Invitational | | 15 | 17:58.00 |
| Riley Smith (Jr.) | Wolverine Invitational | | 3 | 18:12.99 |
| Riley Smith (Jr.) | Chad Smith Scholarship Invitational | | 5 | 18:16.00 |
| Will King (So.) | Shakamak Invitational | | 26 | 18:17.00 |
| Dosson Lamb (So.) | Wolverine Invitational | | 5 | 18:22.00 |
| Riley Smith (Jr.) | THSB 1A-3A | | 4 | 18:22.00 |
| Riley Smith (Jr.) | North Central/Clay City | | 1 | 18:25.00 |
| Riley Smith (Jr.) | Sullivan vs North Knox North Daviess | | 1 | 18:26.00 |
| Preston Anthony (Fr.) | Wolverine Invitational | | 6 | 18:29.00 |
| Riley Smith (Jr.) | Shakamak Invitational | | 33 | 18:31.00 |
| Dosson Lamb (So.) | Western Indiana Conference | | 17 | 18:33.00 |
| Dosson Lamb (So.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 18:35.00 |
| Dosson Lamb (So.) | Chad Smith Scholarship Invitational | | 7 | 18:39.00 |
| Riley Smith (Jr.) | Bloomfield Invite | | 1 | 18:50.00 |
| Preston Anthony (Fr.) | Western Indiana Conference | | 24 | 18:51.00 |
| Dosson Lamb (So.) | North Central (Farmersburg, IN) | | 1 | 18:59.00 |
| Dosson Lamb (So.) | THSB 1A-3A | | 10 | 19:01.00 |
| Will King (So.) | Western Indiana Conference | | 29 | 19:08.00 |
| Will King (So.) | Wolverine Invitational | | 10 | 19:10.00 |
| Riley Smith (Jr.) | West Vigo (West Terre Haute, IN) | | 1 | 19:12.00 |
| Preston Anthony (Fr.) | North Central (Farmersburg, IN) | | 2 | 19:18.00 |
| Riley Smith (Jr.) | Western Indiana Conference | | 34 | 19:18.00 |
| Preston Anthony (Fr.) | North Central/Clay City | | 2 | 19:19.00 |
| Riley Smith (Jr.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 19:25.00 |
| Preston Anthony (Fr.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 19:26.00 |
| Preston Anthony (Fr.) | Chad Smith Scholarship Invitational | | 13 | 19:27.00 |
| Cole Migliorini (Sr.) | Shakamak Invitational | | 44 | 19:28.00 |
| Preston Anthony (Fr.) | THSB 1A-3A | | 17 | 19:31.00 |
| Caden McCrary (So.) | Shakamak Invitational | | | 19:36.00 |
| Grant Alexander (Jr.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 19:37.00 |
| Grant Alexander (Jr.) | North Central/Clay City | | 6 | 19:44.00 |
| Grant Alexander (Jr.) | Chad Smith Scholarship Invitational | | 18 | 19:46.00 |
| Dosson Lamb (So.) | Sullivan vs North Knox North Daviess | | 2 | 19:49.00 |
| Walker Brocksmith (Fr.) | Shakamak Invitational | | 52 | 19:50.00 |
| Dosson Lamb (So.) | Bloomfield Invite | | 5 | 19:57.00 |
| Will King (So.) | North Central (Farmersburg, IN) | | 3 | 19:57.00 |
| Preston Anthony (Fr.) | Sullivan vs North Knox North Daviess | | 3 | 19:58.00 |
| Will King (So.) | North Central/Clay City | | 9 | 20:01.00 |
| Will King (So.) | Chad Smith Scholarship Invitational | | 21 | 20:02.00 |
| Preston Anthony (Fr.) | Bloomfield Invite | | 7 | 20:02.00 |
| Walker Brocksmith (Fr.) | Western Indiana Conference | | 73 | 20:04.00 |
| Dosson Lamb (So.) | West Vigo (West Terre Haute, IN) | | 3 | 20:06.00 |
| Grant Alexander (Jr.) | Sullivan vs North Knox North Daviess | | 4 | 20:06.00 |
| Grant Alexander (Jr.) | Western Indiana Conference | | 52 | 20:16.00 |
| Grant Alexander (Jr.) | THSB 1A-3A | | 26 | 20:16.00 |
| Grant Alexander (Jr.) | West Vigo (West Terre Haute, IN) | | 5 | 20:18.00 |
| Tim Lueking (Fr.) | Shakamak Invitational | | 59 | 20:23.00 |
| Cole Migliorini (Sr.) | North Central/Clay City | | 13 | 20:30.00 |
| Cole Migliorini (Sr.) | Western Indiana Conference | | 58 | 20:31.00 |
| Grant Alexander (Jr.) | Wolverine Invitational | | 17 | 20:36.00 |
| Will King (So.) | West Vigo (West Terre Haute, IN) | | 6 | 20:37.00 |
| Will King (So.) | THSB 1A-3A | | 35 | 20:43.00 |
| Cole Migliorini (Sr.) | North Central (Farmersburg, IN) | | 4 | 20:47.00 |
| Will King (So.) | Sullivan vs North Knox North Daviess | | 7 | 20:52.00 |
| Grant Alexander (Jr.) | Bloomfield Invite | | 12 | 20:55.00 |
| Cole Migliorini (Sr.) | Wolverine Invitational | | 20 | 20:56.00 |
| Cole Migliorini (Sr.) | THSB 1A-3A | | 39 | 20:59.00 |
| Will King (So.) | Bloomfield Invite | | 16 | 21:08.00 |
| Cole Migliorini (Sr.) | Bloomfield Invite | | 17 | 21:13.00 |
| Cole Migliorini (Sr.) | Sullivan vs North Knox North Daviess | | 8 | 21:23.00 |
| Tim Lueking (Fr.) | Chad Smith Scholarship Invitational | | 50 | 21:34.00 |
| Cole Migliorini (Sr.) | Chad Smith Scholarship Invitational | | 51 | 21:35.00 |
| Caden McCrary (So.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 21:36.00 |
| Walker Brocksmith (Fr.) | Chad Smith Scholarship Invitational | | 52 | 21:45.00 |
| Tim Lueking (Fr.) | Western Indiana Conference | | | 21:46.00 |
| Walker Brocksmith (Fr.) | North Central (Farmersburg, IN) | | 6 | 21:53.00 |
| Tim Lueking (Fr.) | Wolverine Invitational | | 26 | 22:04.00 |
| Walker Brocksmith (Fr.) | Wolverine Invitational | | 27 | 22:12.00 |
| Caden McCrary (So.) | Wolverine Invitational | | 28 | 22:21.00 |
| Walker Brocksmith (Fr.) | Sullivan vs North Knox North Daviess | | 10 | 22:38.00 |
| Tim Lueking (Fr.) | Bloomfield Invite | | 23 | 22:42.00 |
| Walker Brocksmith (Fr.) | North Central/Clay City | | 17 | 22:44.00 |
| Cole Migliorini (Sr.) | West Vigo (West Terre Haute, IN) | | 13 | 22:49.00 |
| Tim Lueking (Fr.) | THSB 1A-3A | | 72 | 22:52.00 |
| Walker Brocksmith (Fr.) | THSB 1A-3A | | 76 | 23:01.00 |
| Tim Lueking (Fr.) | North Central (Farmersburg, IN) | | 8 | 23:04.00 |
| Caden McCrary (So.) | Bloomfield Invite | | 27 | 23:17.00 |
| Walker Brocksmith (Fr.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 23:20.00 |
| Caden McCrary (So.) | North Central/Clay City | | 24 | 23:22.00 |
| Caden McCrary (So.) | THSB 1A-3A | | 78 | 23:28.00 |
| Alex Baker (Fr.) | Shakamak Invitational | | | 23:44.00 |
| Walker Brocksmith (Fr.) | West Vigo (West Terre Haute, IN) | | 15 | 24:19.00 |
| Caden McCrary (So.) | North Central (Farmersburg, IN) | | 10 | 24:37.00 |
| Alex Baker (Fr.) | Western Indiana Conference | | | 24:50.00 |
| Alex Baker (Fr.) | THSB 1A-3A | | 103 | 25:49.00 |
| Tim Lueking (Fr.) | North Central/Clay City | | 21 | 25:57.00 |
| Alex Baker (Fr.) | Valley Kickoff Classic Boys Cross Country Meet | Valley Kickoff Classic Boys Cross Country Meet | | 26:34.00 |
| Alex Baker (Fr.) | Sullivan vs North Knox North Daviess | | 15 | 26:53.00 |
| Tim Lueking (Fr.) | West Vigo (West Terre Haute, IN) | | 18 | 27:04.00 |
| Alex Baker (Fr.) | North Central/Clay City | | 26 | 27:28.00 |
| Dalton Rasmussen (Fr.) | Shakamak Invitational | | | 28:08.00 |
| Dalton Rasmussen (Fr.) | Wolverine Invitational | | 37 | 30:27.00 |
| Alex Baker (Fr.) | West Vigo (West Terre Haute, IN) | | 20 | 30:33.00 |
| Dalton Rasmussen (Fr.) | THSB 1A-3A | | 122 | 30:44.00 |
| Dalton Rasmussen (Fr.) | North Central (Farmersburg, IN) | | 17 | 30:58.00 |
| Dalton Rasmussen (Fr.) | Bloomfield Invite | | | 31:39.00 |
| Dalton Rasmussen (Fr.) | Chad Smith Scholarship Invitational | | 102 | 34:31.00 |
| Dalton Rasmussen (Fr.) | Western Indiana Conference | | | 38:15.00 |
