| Rank | # | School | Years | |
| 1 | 26 | Ritenour | 1951-1976 | 399-127 |
| 1 | 26 | Helias Catholic | 1992-2018 | 473-176 |
| 3 | 24 | New Franklin | 1982-2006 | |
| 4 | 20 | Festus | 1998-2018 | |
| 5 | 17 | Holt | 2002-2017 | |
| 5 | 17 | Plato | 2003-2019 | 285-112 |
| 7 | 16 | Helias Catholic | 1992-2007 | |
| 7 | 16 | Holt | 2002-2017 | |
| 9 | 15 | Mansfield | 1987-2001 | |
| 9 | 15 | Holt | 2002-2016 | |
| 11 | 14 | Central (Cape Girardeau) | 1960-1973 | |
| 12 | 12 | Central (Cape Girardeau) | 1985-1996 | |
| 13 | 11 | Central (Park Hills) | 1984-1994 | 177-72 |
| 13 | 11 | Westminster Christian Academy | 2001-2011 | 201-74 |