| Rank | W | Student | School | Years | |
| 1 | 72 | | North Harrison | 1989-1998 | |
| 2 | 46 | | Sullivan | 2007-2014 | |
| 3 | 35 | | Jefferson (Conception Jct.) | 1995-2002 | |
| 4 | 32 | | Bevier | 2003-2006 | |
| 5 | 31 | | Kirksville | 2007-2010 | |
| 6 | 29 | | Putnam County | 1988-1992 | |
| 7 | 24 | | Lathrop | 2015-2019 | |
| 7 | 24 | | Trenton | 2016-2018 | |
| 9 | 23 | | Jefferson (Conception Jct.) | 1991-1994 | |
| 9 | 23 | | North Harrison | 1999-2002 | |
| 9 | 23 | | Palmyra | 2006-2010 | |
| 9 | 23 | | Holt | 2014-2017 | |