| Ryan Ault (Jr.) | 2019 IHSAA Columbus North Regional Boys Cross County Meet | | 18 | 16:44.50 |
| Ryan Ault (Jr.) | Whiteland Invitational | Boys Varsity | 8 | 17:16.35 |
| Ryan Ault (Jr.) | 2019 IHSAA Brown County Sectional Boys Cross Country Mee | 2019 IHSAA Brown County Sectional Boys Cross Country Meet | 18 | 17:36.38 |
| Ryan Ault (Jr.) | Greensburg Invite | | 4 | 17:47.79 |
| Ryan Ault (Jr.) | Morristown (IN) | | 1 | 17:49.00 |
| Ryan Ault (Jr.) | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 2019 IHSAA Brown County Boys Semi-State Cross Country Meet | 104 | 17:49.20 |
| Ryan Ault (Jr.) | Mid-Hoosier Conference | | 2 | 17:52.12 |
| Ryan Ault (Jr.) | East Central Invite | Division II Boys | 2 | 17:54.40 |
| Ryan Ault (Jr.) | Indian Creek Invitational | | 5 | 18:00.27 |
| Ryan Ault (Jr.) | Heritage Days Classic | | 1 | 18:14.00 |
| Noah Estes (Fr.) | Whiteland Invitational | Boys Varsity | 42 | 19:04.35 |
| Ryan Ault (Jr.) | Hauser / South Decatur / Greensburg | | 2 | 19:17.00 |
| Alex Bower (Fr.) | 2019 IHSAA Brown County Sectional Boys Cross Country Mee | 2019 IHSAA Brown County Sectional Boys Cross Country Meet | 46 | 19:24.10 |
| Ryan Ault (Jr.) | Austin Invitational | | 26 | 19:25.08 |
| Noah Estes (Fr.) | Heritage Days Classic | | 2 | 19:38.00 |
| Noah Estes (Fr.) | Mid-Hoosier Conference | | 6 | 19:38.17 |
| Alex Bower (Fr.) | Heritage Days Classic | | 4 | 19:47.00 |
| Alex Bower (Fr.) | Whiteland Invitational | Boys Varsity | 57 | 20:03.39 |
| Noah Estes (Fr.) | East Central Invite | Division II Boys | 15 | 20:06.10 |
| Cameron Toole (Fr.) | 2019 IHSAA Brown County Sectional Boys Cross Country Mee | 2019 IHSAA Brown County Sectional Boys Cross Country Meet | 51 | 20:11.53 |
| Noah Estes (Fr.) | Hauser / South Decatur / Greensburg | | 8 | 20:12.00 |
| Noah Estes (Fr.) | Indian Creek Invitational | | 23 | 20:13.57 |
| Tanner Ault (Fr.) | Whiteland Invitational | Boys Varsity | 60 | 20:15.81 |
| Noah Estes (Fr.) | Morristown (IN) | | 2 | 20:19.00 |
| Noah Estes (Fr.) | Greensburg Invite | | 35 | 20:19.51 |
| Tanner Ault (Fr.) | Heritage Days Classic | | 6 | 20:22.00 |
| Alex Bower (Fr.) | Greensburg Invite | | 40 | 20:24.50 |
| Alex Bower (Fr.) | East Central Invite | Division II Boys | 22 | 20:29.70 |
| Tanner Ault (Fr.) | Morristown (IN) | | 3 | 20:31.00 |
| Alex Bower (Fr.) | Mid-Hoosier Conference | | 11 | 20:31.33 |
| Cameron Toole (Fr.) | Heritage Days Classic | | 7 | 20:32.00 |
| Alex Bower (Fr.) | Morristown (IN) | | 4 | 20:51.00 |
| Cameron Toole (Fr.) | Whiteland Invitational | Boys Varsity | 65 | 20:57.17 |
| Tanner Ault (Fr.) | Mid-Hoosier Conference | | 13 | 21:17.03 |
| Cameron Toole (Fr.) | Mid-Hoosier Conference | | 15 | 21:23.89 |
| Alex Bower (Fr.) | Austin Invitational | | 37 | 21:27.62 |
| Tanner Ault (Fr.) | Greensburg Invite | | 59 | 21:31.63 |
| Cameron Toole (Fr.) | East Central Invite | Division II Boys | 31 | 21:39.30 |
| Alex Bower (Fr.) | Indian Creek Invitational | | 37 | 21:47.41 |
| Alex Bower (Fr.) | Hauser / South Decatur / Greensburg | | 12 | 21:56.00 |
| Cameron Toole (Fr.) | Greensburg Invite | | 67 | 22:15.86 |
| Noah Estes (Fr.) | Austin Invitational | | 40 | 22:22.19 |
| Tanner Ault (Fr.) | East Central Invite | Division II Boys | 37 | 22:42.40 |
| Tanner Ault (Fr.) | 2019 IHSAA Brown County Sectional Boys Cross Country Mee | 2019 IHSAA Brown County Sectional Boys Cross Country Meet | 57 | 23:00.03 |
| Cameron Toole (Fr.) | Morristown (IN) | | 8 | 23:47.00 |
| Tanner Ault (Fr.) | Hauser / South Decatur / Greensburg | | 22 | 24:57.00 |
| Cameron Toole (Fr.) | Hauser / South Decatur / Greensburg | | 24 | 25:57.00 |
| Aiden Cheshire (Fr.) | East Central Invite | Division II Boys | 47 | 26:32.60 |
| Aiden Cheshire (Fr.) | 2019 IHSAA Brown County Sectional Boys Cross Country Mee | 2019 IHSAA Brown County Sectional Boys Cross Country Meet | 65 | 27:59.65 |
| Cameron Toole (Fr.) | Austin Invitational | | 52 | 29:06.06 |
| Aiden Cheshire (Fr.) | Indian Creek Invitational | | 51 | 29:22.44 |
| Aiden Cheshire (Fr.) | Hauser / South Decatur / Greensburg | | 29 | 30:37.00 |