| YEAR | CHAMPION | RUNNER-UP | VENUE | SCORE |
|---|---|---|---|---|
| 1991 | Don Bliss | Terry Tessary | CC at the Legends | 218 |
| 1992 | Derre Owsley | David Lucks | Bogey Hills CC | 214 |
| 1993 | Don Bliss | Barry Yehling | Lake Forest G&CC | 213 |
| 1994 | Jim Holtgrieve |
Don Bliss David Estes |
CC of St. Albans (Lewis & Clark) | 217 |
| 1995 | Craig Schnurbusch | Jim Mason | Spencer T. Olin GC | 211 |
| 1996 | Tom Barry | David Estes | Bellerive CC | 213 |
| 1997 | David Estes | Craig Schnurbusch | Fox Run GC | 214 |
| 1998 | David Estes |
Jim Holtgrieve |
Old Warson CC | 214 |
| 1999 | Brian Kennedy |
Phil Caravia David Estes Doug Diemer |
Norwood Hills CC (West) | 215 |
| 2000 | Bob Beckmann | Tom Barry | Meadowbrook CC | 216 |
| 2001 | Scott Fann | Scott Thomas | Gateway National GL | 207 |
| 2002 | Mike Sabo | David Lucks | Westwood CC | 209 |
| 2003 | Scott Edwards + | Shawn Jasper | Persimmon Woods GC | 216 |
| 2004 | John Kelly | Darren Lundgren | Glen Echo CC | 207 |
| 2005 | Parker LaBarge | Darren Lundgren | Fox Run GC | 212 |
| 2006 | Darren Lundgren + | Parker LaBarge | Boone Valley GC | 217 |
| 2007 | Ryan Franks | Scott Langley | WingHaven CC | 213 |
| 2008 | Adam Long | Skip Berkmeyer | Norwood Hills CC (West) | 211 |
| 2009 | Skip Berkmeyer | Ted Moloney | Bellerive CC | 214 |
| 2010 | Eli Grant | Brian Craig | Meadowbrook CC | 215 |
| 2011 | Ryan Penfield | Ben Crancer | St. Louis CC | 214 |
| 2012 | Kyle Weldon |
Kevin Bell Skip Berkmeyer |
Old Warson CC | 209 |
| 2013 | Kyle Weldon | Phil Caravia | Persimmon Woods GC | 208 |
| 2014 | Teddy Jones + |
John Anderson Patrick Riordan |
Westwood CC | 212 |
| 2015 | Jimmy Siegfried + | Skip Berkmeyer | Boone Valley GC | 216 |
| 2016 | Andrew Pranger |
Darren Stoffel Tony Gumper |
Glen Echo CC | 210 |
| 2017 | Shawn Jasper | Ryan Eckelkamp | Norwood Hills CC (West) | 214 |
| 2018 | Andrew Pranger |
Skip Berkmeyer Crimson Callahan |
CC of St. Albans (Lewis & Clark) | 211 |
| 2019 | Brad Carpenter | Curtis Brokenbrow | Aberdeen GC | 206 |
| 2020 | Chris Ferris | Chris Kovach | Meadowbrook CC | 210 |
| 2021 | Nick Westrich | Curtis Brokenbrow | St. Louis CC | 205 |
| + Won in Playoff |