| Owen Sprinkle (Jr.) | Rick Weinheimer Cross Country Classic | varsity class a | 34 | 18:21.00 |
| Owen Sprinkle (Jr.) | Brown County Eagle Classic | Class A | 26 | 18:24.70 |
| Jack Baker (Sr.) | 2020 IHSAA Mt. Vernon Sectional Boys Cross Country | | 34 | 18:33.20 |
| Owen Sprinkle (Jr.) | Eastern Hancock Invitational | | 5 | 18:37.30 |
| Jack Baker (Sr.) | Rick Weinheimer Cross Country Classic | varsity class a | 53 | 18:47.30 |
| Jack Baker (Sr.) | Brown County Eagle Classic | Class A | 37 | 18:59.80 |
| Owen Sprinkle (Jr.) | Indiana Crossroads Conference | | 15 | 19:09.43 |
| Jack Baker (Sr.) | Shelby County | | 3 | 19:20.61 |
| Jack Baker (Sr.) | Shelbyville High School | Gold Division | 42 | 19:25.40 |
| Owen Sprinkle (Jr.) | 2020 IHSAA Mt. Vernon Sectional Boys Cross Country | | 43 | 19:34.40 |
| Jack Baker (Sr.) | Early Bird XC Invitational | Early Bird Invite | 6 | 19:38.69 |
| Owen Sprinkle (Jr.) | Jeremy Wright Memorial Small School Invitational | | 32 | 19:46.66 |
| Jack Baker (Sr.) | Indiana Crossroads Conference | | 24 | 20:10.37 |
| Jack Baker (Sr.) | Jeremy Wright Memorial Small School Invitational | | 44 | 20:15.49 |
| Owen Sprinkle (Jr.) | Early Bird XC Invitational | Early Bird Invite | 18 | 20:55.65 |
| Davis Helm (Sr.) | Shelby County | | 12 | 22:19.25 |
| Davis Helm (Sr.) | Brown County Eagle Classic | Class A | 91 | 22:33.70 |
| Davis Helm (Sr.) | Rick Weinheimer Cross Country Classic | varsity class a | 161 | 22:34.20 |
| Davis Helm (Sr.) | Shelbyville High School | Gold Division | 85 | 22:35.30 |
| Davis Helm (Sr.) | Indiana Crossroads Conference | | 42 | 22:46.76 |
| Lucas Bear (Jr.) | Brown County Eagle Classic | Class A | 93 | 22:52.20 |
| Davis Helm (Sr.) | Eastern Hancock Invitational | | 44 | 23:18.08 |
| Lucas Bear (Jr.) | Shelby County | | 14 | 23:19.07 |
| Lucas Bear (Jr.) | Shelbyville High School | Gold Division | 88 | 23:30.90 |
| Lucas Bear (Jr.) | 2020 IHSAA Mt. Vernon Sectional Boys Cross Country | | 70 | 23:41.50 |
| Lucas Bear (Jr.) | Eastern Hancock Invitational | | 46 | 23:42.30 |
| Lucas Bear (Jr.) | Indiana Crossroads Conference | | 52 | 24:45.44 |
| Lucas Bear (Jr.) | Rick Weinheimer Cross Country Classic | varsity class a | 176 | 24:47.40 |
| Davis Helm (Sr.) | Jeremy Wright Memorial Small School Invitational | | 178 | 24:56.50 |
| Davis Helm (Sr.) | Early Bird XC Invitational | Early Bird Invite | 28 | 25:14.79 |
| Corbin Maurice (Jr.) | Shelby County | | 18 | 25:33.78 |
| Corbin Maurice (Jr.) | Eastern Hancock Invitational | | 54 | 25:37.54 |
| Corbin Maurice (Jr.) | Indiana Crossroads Conference | | 54 | 25:53.54 |
| Lucas Bear (Jr.) | Jeremy Wright Memorial Small School Invitational | | 188 | 25:57.98 |
| Corbin Maurice (Jr.) | Rick Weinheimer Cross Country Classic | varsity class a | 180 | 25:58.90 |
| Corbin Maurice (Jr.) | Shelbyville High School | Gold Division | 98 | 26:13.20 |
| Corbin Maurice (Jr.) | Brown County Eagle Classic | Class A | 103 | 26:38.90 |
| Lucas Bear (Jr.) | Early Bird XC Invitational | Early Bird Invite | 30 | 27:58.11 |
| Jaxon Graves (Jr.) | Early Bird XC Invitational | Early Bird Invite | 34 | 28:05.67 |
| Corbin Maurice (Jr.) | Early Bird XC Invitational | Early Bird Invite | 31 | 28:05.67 |
| Corbin Maurice (Jr.) | Jeremy Wright Memorial Small School Invitational | | 212 | 29:24.07 |
| Jaxon Graves (Jr.) | Rick Weinheimer Cross Country Classic | varsity class a | 183 | 32:00.50 |
| Jaxon Graves (Jr.) | Brown County Eagle Classic | Class A | 105 | 33:40.20 |
| Joe Weir (So.) | Jeremy Wright Memorial Small School Invitational | | 224 | 38:34.45 |
| Joe Weir (So.) | Brown County Eagle Classic | Class A | 106 | 40:40.00 |
| Joe Weir (So.) | Eastern Hancock Invitational | | 59 | 41:16.80 |
