| Year | Champion | Tournament Site (City) |
| 1993 | Tom Studer | Crystal Lake CC (Crystal Lake) |
| 1994 | Stephen Daly | Royal Fox CC (St. Charles) |
| 1995 | Stephen Daly | Prairie Landing GC (West Chicago) |
| 1996 | Richard Dukelow | Balmoral Woods GC (Crete) |
| 1997 | Michael Stone | Eagle Ridge Resort (Galena) |
| 1998 | Richard Dukelow | Schaumburg GC (Schaumburg) |
| 1999 | Mark Esposito | White Eagle GC (Naperville) |
| 2000 | Michael Stone | White Eagle GC (Naperville) |
| 2001 | Tim Scott | White Eagle GC (Naperville) |
| 2002 | Curtis Minkel | White Eagle GC (Naperville) |
| 2003 | Dave Ryan | White Eagle GC (Naperville) |
| 2004 | Rick LeHew | White Eagle GC (Naperville) |
| 2005 | Tom Miler | White Eagle GC (Naperville) |
| 2006 | Mark Esposito | White Eagle GC (Naperville) |
| 2007 | John Ehrgott | White Eagle GC (Naperville) |
| 2008 | Todd Mitchell | White Eagle GC (Naperville) |
| *2009 | John Ehrgott | White Eagle GC (Naperville) |
| 2010 | Todd Mitchell | White Eagle GC (Naperville) |
| 2011 | Todd Mitchell | Flossmoor CC (Flossmoor) |
| 2012 | Kyle Nathan | Flossmoor CC (Flossmoor) |
| 2013 |
Todd Mitchell | Flossmoor CC (Flossmoor) |
| 2014 |
Andrew Price
| Flossmoor CC (Flossmoor) |
| 2015 |
Chadd Slutzky | Flossmoor CC (Flossmoor) |
| 2016 |
Todd Mitchell
| Flossmoor CC (Flossmoor) |
| 2017 |
Greg Bauman | Exmoor CC (Highland Park) |
| 2018 |
Logan Stauffer
| Glen Oak CC (Glen Ellyn) |
| 2019 | Chadd Slutzky
| Stonebridge CC (Aurora) |
| 2020 | John Ramsey
| Edgewood Valley CC (La Grange) |
| 2021 |
Larry Blatt
| Bloomington CC (Bloomington) |
| 2022 |
Chadd Slutzky
| Evanston GC (Skokie) |
| 2023 |
Will Hickey
| Biltmore CC (North Barrington) |
| 2024 |
| Park Ridge CC (Park Ridge) |
