| Rank | Name | Year | Meet(Location) | Time |
| 1 | Lilly Lacy | 2017 | Eagle Classic (Brown County) | 19:27 |
| 2 | Morgan McCarter | 2011 | Regional (Greensburg HS) | 19:30 |
| 3 | Kyleigh Brown | 2008 | Regional (Greensburg HS) | 19:46 |
| 4 | Jenna Newton | 2018 | Semi-State (Shelbyville) | 20:15 |
| 5 | Katie Smith | 2010 | Regional (Greensburg HS) | 20:23 |
| Traci Smith | 2010 | Regional (Greensburg HS) | 20:23 | |
| 7 | Meagan Hash | 2009 | Sectional (JCHP) | 20:30 |
| 8 | Haley Anderson | 2007 | Regional (Greensburg HS) | 20:33 |
| 9 | Hanna Moore | 2008 | Flashrock (Carmel) | 20:34 |
| 10 | Kylie Kireta | 2008 | Flashrock (Carmel) | 20:39 |
| 11 | Kyana Kemp | 2008 | Johnson County (JCHP) | 20:40 |
| 12 | Zoe Piotrowski | 2012 | Regional (Greensburg HS) | 20:43 |
| 13 | Eran Treibic | 2019 | Johnson County (FCHS) | 20:58 |
| 14 | Alexandra Boardman | 2015 | Mid-State (Decatur Central) | 21:03 |
| 15 | Kendyl Harrison | 2015 | Mid-State (Decatur Central) | 21:17 |
| 16 | Chloe Selking | 2015 | Regional (Shelbyville) | 21:24 |
| 17 | Katie Hotopp | 2012 | Johnson County (FCHS) | 21:35 |
| 18 | Shelby Parmer | 2008 | Flashrock (Carmel) | 21:37 |
| 19 | Emma Treibic | 2014 | Eagle Classic (Brown County) | 21:43 |
| Mallory Luse | 2019 | Johnson County (FCHS) | 21:43 |
| Rank | Name | Year | Meet(Location) | Time |
| 1 | Brad Wheeler | 2000 | Semi-State (SE. Park) | 16:16 |
| 2 | Sean Wilson | 2004 | Johnson County (JCHP) | 16:19 |
| 3 | Andrew Bixler | 2015 | Regional (Shelbyville) | 16:25 |
| 4 | Ryan Warrenburg | 1998 | Mid-State (JCHP) | 16:37 |
| 5 | Ricky Warren | 2004 | Johnson County (JCHP) | 16:38 |
| 6 | Joey Shepard | 1999 | Mid-State (JCHP) | 16:42 |
| 7 | Zach Tranter | 2005 | Sectional (JCHP) | 16:43 |
| 8 | Jeff Powers | 1998 | Mid-State (JCHP) | 16:45 |
| Brandon Griffin | 1999 | Sectional (JCHP) | 16:45 | |
| 10 | Andy Snyder | 1994 | Franklin Central Inv. (SE Park) | 16:46 |
| 11 | Isaiah Lindsay | 2015 | Regional (Shelbyville) | 16:51 |
| 12 | Brandon Smith | 2001 | Sectional (JCHP) | 16:58 |
| 13 | Josh Campbell | 2014 | Mid-State (FCHS) | 17:00 |
| 14 | Jared Cambell | 2000 | Semi-State (SE. Park) | 17:02 |
| 15 | Colin Riessen | 1998 | Mid-State (JCHP) | 17:03 |
| 16 | Jeremy Coy | 1994 | Mid-State (Plainfield) | 17:07 |
| 17 | Anthony McDonald | 2017 | Semi-State (Shelbyville) | 17:08 |
| 18 | Camden MacLennan | 2010 | Johnson County (JCHP) | 17:22 |
| 19 | Kevan Pangburn | 2002 | Franklin Central Inv. (SE Park) | 17:25 |
| 20 | Josh Ford | 2010 | Johnson County (JCHP) | 17:32 |