| Rank | Total | Student | School | Years |
| 1 | 3 |
Eugene Fehlig
SLUH
| SLUH | 1936, 1937, 1938 |
| 1 | 3 |
Jack Parker
Father Tolton Regional Catholic
| Father Tolton Regional Catholic | 2013, 2015, 2016 |
| 3 | 2 |
Don Guariglia
Normandy Collaborative
| Normandy Collaborative | 1949, 1950 |
| 3 | 2 |
Elliot Pachter
Pembroke Hill
| Pembroke Hill | 1960, 1961 |
| 3 | 2 |
Tom Watson
Pembroke Hill
| Pembroke Hill | 1965, 1966 |
| 3 | 2 |
Chris Collins
Arcadia Valley
| Arcadia Valley | 1985, 1986 |
| 3 | 2 |
Doug Diemer
Priory
| Priory | 1990, 1992 |
| 3 | 2 |
Pedren Alumbaugh
Sarcoxie
| Sarcoxie | 1991, 1992 |
| 3 | 2 |
Colby Robertson
Poplar Bluff
| Poplar Bluff | 1993, 1995 |
| 3 | 2 |
Mike Sabo
Chaminade College Prep
| Chaminade College Prep | 1996, 1997 |
| 3 | 2 |
Dean Merrill
Pembroke Hill
| Pembroke Hill | 2001, 2002 |
| 3 | 2 |
Connor McHenry
Helias Catholic
| Helias Catholic | 2004, 2005 |
| 3 | 2 |
Jared Essary
Galena
| Galena | 2004, 2006 |
| 3 | 2 |
Jace Long
Dixon
| Dixon | 2006, 2007 |
| 3 | 2 |
Ryan Zech
Kearney
| Kearney | 2008, 2010 |
| 3 | 2 |
Mike Wootten
Francis Howell
| Francis Howell | 2010, 2011 |
| 3 | 2 |
Mitchell Rutledge
Whitfield
| Whitfield | 2010, 2011 |
| 3 | 2 |
Brett Windsor
Boonville
| Boonville | 2013, 2014 |
| 3 | 2 |
Jack Litzelfelner
Notre Dame (Cape Girardeau)
| Notre Dame (Cape Girardeau) | 2012, 2015 |
| 3 | 2 |
Ryan Joon Lee
Pembroke Hill
| Pembroke Hill | 2018, 2020 |
| 3 | 2 |
Quinn Thomas
Hannibal
| Hannibal | 2020, 2023 |
| 3 | 2 |
Trigg Lindahl
Hermann
| Hermann | 2021, 2023 |
| 3 | 2 |
John (Bubba) Chapman
Chaminade College Prep
| Chaminade College Prep | 2022, 2023 |
| 3 | 2 |
Peyton Smith
Summit Christian Academy
| Summit Christian Academy | 2022, 2023 |