| Ryan Ault (Sr.) | Morristown (IN) | | 1 | 17:40.00 |
| Ryan Ault (Sr.) | Mid-Hoosier Conference | | 1 | 17:45.84 |
| Ryan Ault (Sr.) | Greensburg Invitational | | 4 | 17:48.04 |
| Ryan Ault (Sr.) | Heritage Days Classic | | 1 | 17:52.00 |
| Ryan Ault (Sr.) | Whiteland Invitational | | 9 | 17:54.39 |
| Ryan Ault (Sr.) | South Decatur Invitational | | 1 | 18:01.00 |
| Ryan Ault (Sr.) | 2020 IHSAA Columbus North Regional Boys Cross Country Meet | | 43 | 18:18.30 |
| Ryan Ault (Sr.) | 2020 IHSAA Brown County Sectional Boys Cross Country Meet | | 21 | 18:22.50 |
| Ryan Ault (Sr.) | East Central Invitational | Division II | 2 | 18:26.80 |
| Ryan Ault (Sr.) | Jeremy Wright Memorial Small School Invitational | | 10 | 18:32.05 |
| Ryan Ault (Sr.) | Hauser / South Decatur / Greensburg | | 1 | 18:43.00 |
| Alex Bower (So.) | Morristown (IN) | | 2 | 18:52.00 |
| Alex Bower (So.) | 2020 IHSAA Columbus North Regional Boys Cross Country Meet | | 58 | 18:57.50 |
| Alex Bower (So.) | Greensburg Invitational | | 30 | 19:07.84 |
| Colin Kistler (Fr.) | Morristown (IN) | | 3 | 19:12.00 |
| Ryan Ault (Sr.) | Hauser Jets Invitational | | 3 | 19:21.00 |
| Alex Bower (So.) | Whiteland Invitational | | 34 | 19:24.62 |
| Alex Bower (So.) | Heritage Days Classic | | 7 | 19:28.00 |
| Alex Bower (So.) | 2020 IHSAA Brown County Sectional Boys Cross Country Meet | | 41 | 19:54.50 |
| Alex Bower (So.) | East Central Invitational | Division II | 10 | 19:55.10 |
| Colin Kistler (Fr.) | Heritage Days Classic | | 12 | 19:59.00 |
| Tanner Ault (So.) | Greensburg Invitational | | 38 | 20:00.59 |
| Alex Bower (So.) | Mid-Hoosier Conference | | 9 | 20:00.62 |
| Colin Kistler (Fr.) | Whiteland Invitational | | 45 | 20:00.92 |
| Colin Kistler (Fr.) | Greensburg Invitational | | 39 | 20:01.12 |
| Alex Bower (So.) | Hauser Jets Invitational | | 9 | 20:05.00 |
| Colin Kistler (Fr.) | East Central Invitational | Division II | 12 | 20:05.70 |
| Colin Kistler (Fr.) | Mid-Hoosier Conference | | 10 | 20:06.24 |
| Tanner Ault (So.) | Morristown (IN) | | 4 | 20:10.00 |
| Colin Kistler (Fr.) | 2020 IHSAA Brown County Sectional Boys Cross Country Meet | | 44 | 20:16.10 |
| Tanner Ault (So.) | Mid-Hoosier Conference | | 11 | 20:16.40 |
| Cameron Toole (So.) | Mid-Hoosier Conference | | 12 | 20:17.51 |
| Colin Kistler (Fr.) | Hauser / South Decatur / Greensburg | | 9 | 20:37.00 |
| Alex Bower (So.) | South Decatur Invitational | | 14 | 20:40.00 |
| Alex Bower (So.) | Jeremy Wright Memorial Small School Invitational | | 64 | 20:42.86 |
| Colin Kistler (Fr.) | South Decatur Invitational | | 15 | 20:43.00 |
| Alex Bower (So.) | Hauser / South Decatur / Greensburg | | 10 | 20:56.00 |
| Colin Kistler (Fr.) | Hauser Jets Invitational | | 13 | 21:04.00 |
| Colin Kistler (Fr.) | Jeremy Wright Memorial Small School Invitational | | 94 | 21:32.75 |
| Cameron Toole (So.) | Whiteland Invitational | | 63 | 21:34.19 |
| Cameron Toole (So.) | Hauser Jets Invitational | | 20 | 21:59.00 |
| Cameron Toole (So.) | Jeremy Wright Memorial Small School Invitational | | 138 | 22:43.72 |
| Cameron Toole (So.) | East Central Invitational | Division II | 35 | 22:46.30 |
| Aiden Cheshire (So.) | Morristown (IN) | | 5 | 22:54.00 |
| Cameron Toole (So.) | Hauser / South Decatur / Greensburg | | 19 | 23:00.00 |
| Cameron Toole (So.) | South Decatur Invitational | | 36 | 23:09.00 |
| Austin Cowan (So.) | Mid-Hoosier Conference | | 33 | 23:25.64 |
| Austin Cowan (So.) | Whiteland Invitational | | 75 | 24:13.79 |
| Aiden Cheshire (So.) | Heritage Days Classic | | 38 | 24:40.00 |
| Aiden Cheshire (So.) | Greensburg Invitational | | 76 | 24:50.54 |
| Austin Cowan (So.) | South Decatur Invitational | | 44 | 25:28.00 |
| Austin Cowan (So.) | Jeremy Wright Memorial Small School Invitational | | 196 | 26:54.81 |
| Austin Cowan (So.) | Hauser Jets Invitational | | 35 | 27:12.00 |
| Aiden Cheshire (So.) | Jeremy Wright Memorial Small School Invitational | | 215 | 31:57.21 |
