| Benjamin Mckinley (Jr.) | North Central (Farmersburg, IN) | | 2 | 19:52.00 |
| Benjamin Mckinley (Jr.) | Shakamak Invitational | | 20 | 20:01.00 |
| Benjamin Mckinley (Jr.) | Tiger Cub Invite | | 17 | 20:12.00 |
| Keaton Toth (Fr.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 43 | 20:14.00 |
| Benjamin Mckinley (Jr.) | Nike Twilight | Open | 224 | 20:18.00 |
| Benjamin Mckinley (Jr.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 47 | 20:26.00 |
| Keaton Toth (Fr.) | Nike Twilight | Open | 234 | 20:29.00 |
| Keaton Toth (Fr.) | Shakamak Invitational | | 24 | 20:40.00 |
| Benjamin Mckinley (Jr.) | Washington Invite | | 31 | 20:43.00 |
| Benjamin Mckinley (Jr.) | Clay City Invite | | | 20:46.00 |
| Kaden Helms (So.) | Nike Twilight | Open | 248 | 20:53.00 |
| Benjamin Mckinley (Jr.) | The Hometown Savings Bank State Preview | 1A-3A | 52 | 20:57.00 |
| Keaton Toth (Fr.) | Tiger Cub Invite | | 22 | 21:00.00 |
| Keaton Toth (Fr.) | North Central (Farmersburg, IN) | | 3 | 21:01.00 |
| Keaton Toth (Fr.) | Washington Invite | | 35 | 21:02.00 |
| Benjamin Mckinley (Jr.) | Riverton Parke | | 25 | 21:02.00 |
| Keaton Toth (Fr.) | Riverton Parke | | 26 | 21:05.00 |
| Benjamin Mckinley (Jr.) | Chad Smith Invite | | 15 | 21:16.00 |
| Benjamin Mckinley (Jr.) | North Knox (Bicknell, IN) | | 1 | 21:21.00 |
| Keaton Toth (Fr.) | The Hometown Savings Bank State Preview | 1A-3A | 68 | 21:40.00 |
| Benjamin Mckinley (Jr.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 285 | 21:47.00 |
| Benjamin Mckinley (Jr.) | Western Indiana Conference | | 47 | 21:51.00 |
| Keaton Toth (Fr.) | Chad Smith Invite | | 25 | 22:10.00 |
| Keaton Toth (Fr.) | North Knox (Bicknell, IN) | | 2 | 22:12.00 |
| Kaden Helms (So.) | Shakamak Invitational | | 29 | 22:12.00 |
| Keaton Toth (Fr.) | Clay City Invite | | | 22:14.00 |
| Benjamin Mckinley (Jr.) | West Vigo (West Terre Haute, IN) | | 3 | 22:18.00 |
| Kaden Helms (So.) | North Central (Farmersburg, IN) | | 5 | 22:40.00 |
| Kaden Helms (So.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 64 | 22:47.00 |
| Jeremy Salesman (So.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 307 | 22:56.00 |
| Keaton Toth (Fr.) | Western Indiana Conference | | 51 | 22:57.00 |
| Kaden Helms (So.) | Tiger Cub Invite | | 31 | 23:08.00 |
| Kaden Helms (So.) | Clay City Invite | | | 23:13.00 |
| Zack Gibbs (So.) | North Central (Farmersburg, IN) | | 6 | 23:23.00 |
| Zack Gibbs (So.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 68 | 23:23.00 |
| Kaden Helms (So.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 314 | 23:24.00 |
| Kaden Helms (So.) | Western Indiana Conference | | 54 | 23:25.00 |
| Kaden Helms (So.) | Riverton Parke | | 55 | 23:30.00 |
| Zack Gibbs (So.) | Shakamak Invitational | | 32 | 23:30.00 |
| Keaton Toth (Fr.) | West Vigo (West Terre Haute, IN) | | 6 | 23:39.00 |
| Chad Mccammon (Jr.) | North Central (Farmersburg, IN) | | 7 | 23:50.00 |
| Kaden Helms (So.) | Washington Invite | | 70 | 24:00.00 |
| Chad Mccammon (Jr.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 70 | 24:02.00 |
| Kaden Helms (So.) | The Hometown Savings Bank State Preview | 1A-3A | 112 | 24:10.00 |
| Chad Mccammon (Jr.) | Nike Twilight | Open | 301 | 24:11.00 |
| Chad Mccammon (Jr.) | Riverton Parke | | 66 | 24:24.00 |
| Kaden Helms (So.) | Chad Smith Invite | | 44 | 24:29.00 |
| Kaden Helms (So.) | West Vigo (West Terre Haute, IN) | | 7 | 24:33.00 |
| Kaden Helms (So.) | North Knox (Bicknell, IN) | | 7 | 24:53.00 |
| Chad Mccammon (Jr.) | Shakamak Invitational | | 34 | 25:04.00 |
| Chad Mccammon (Jr.) | Tiger Cub Invite | | 38 | 25:12.00 |
| Chad Mccammon (Jr.) | Washington Invite | | 79 | 25:14.00 |
| Jacob Chastain (Jr.) | Tiger Cub Invite | | 39 | 25:22.00 |
| Chad Mccammon (Jr.) | The Hometown Savings Bank State Preview | 1A-3A | 121 | 25:38.00 |
| Zack Gibbs (So.) | Chad Smith Invite | | 48 | 25:41.00 |
| Jacob Chastain (Jr.) | 2022 IHSAA Boys Terre Haute North Sectional Cross Country Meet | | 72 | 26:04.00 |
| Jacob Chastain (Jr.) | Riverton Parke | | 68 | 26:11.00 |
| Zack Gibbs (So.) | The Hometown Savings Bank State Preview | 1A-3A | 124 | 26:11.00 |
| Chad Mccammon (Jr.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 339 | 26:12.00 |
| Jacob Chastain (Jr.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 338 | 26:12.00 |
| Chad Mccammon (Jr.) | Chad Smith Invite | | 52 | 26:17.00 |
| Jacob Chastain (Jr.) | Washington Invite | | 86 | 26:18.00 |
| Jacob Chastain (Jr.) | Chad Smith Invite | | 53 | 26:20.00 |
| Chad Mccammon (Jr.) | Clay City Invite | | | 26:26.00 |
| Chad Mccammon (Jr.) | North Knox (Bicknell, IN) | | 9 | 26:29.00 |
| Chad Mccammon (Jr.) | West Vigo (West Terre Haute, IN) | | 8 | 26:32.00 |
| Jacob Chastain (Jr.) | West Vigo (West Terre Haute, IN) | | 9 | 26:56.00 |
| Jacob Chastain (Jr.) | North Knox (Bicknell, IN) | | 10 | 27:03.00 |
| Jacob Chastain (Jr.) | Clay City Invite | | | 27:15.00 |
| Zack Gibbs (So.) | Clay City Invite | | | 27:17.00 |
| Jacob Chastain (Jr.) | The Hometown Savings Bank State Preview | 1A-3A | 134 | 27:21.00 |
| Zack Gibbs (So.) | West Vigo (West Terre Haute, IN) | | 10 | 27:50.00 |
| Zack Gibbs (So.) | Valley Cross Kickoff Boys Cross Country Meet | 2022 Valley Cross Kickoff Boys Cross Country Meet | 342 | 28:20.00 |
| Zack Gibbs (So.) | Washington Invite | | 89 | 28:34.00 |
| Zack Gibbs (So.) | Western Indiana Conference | | 61 | 28:47.00 |
| Zack Gibbs (So.) | North Knox (Bicknell, IN) | | 11 | 30:56.00 |
| Chad Mccammon (Jr.) | Western Indiana Conference | | 62 | 31:40.00 |
