Thomas O. Sobbe Cup Champions
| Year | Champion | Runner-Up |
|---|---|---|
| 1994 | Bellerive CC | |
| 1995 | Sunset Hills CC | |
| 1996 | Crystal Highlands GC | |
| 1997 | Norwood Hills CC | |
| 1998 | Meadowbrook CC | |
| 1999 | Norwood Hills CC | |
| 2000 | Norwood Hills CC | |
| 2001 | Mid-Rivers GC | |
| 2002 | Franklin County CC | |
| 2003 | Persimmon Woods GC | Norwood Hills CC |
| 2004 | Forest Hills CC | Norwood Hills CC |
| 2005 | Missouri Bluffs GC | CC of St. Albans |
| 2006 | Meadowbrook CC | Old Hickory GC |
| 2007 | Bellerive CC | Meadowbrook CC |
| 2008 | Bellerive CC | Fox Run GC |
| 2009 | Bellerive CC | Fox Run GC |
| 2010 | Bellerive CC | Quincy CC |
| 2011 | Meadowbrook CC | Bellerive CC |
| 2012 | Old Warson CC | Meadowbrook CC |
| 2013 | Glen Echo CC | Norwood Hills CC |
| 2014 | Joachim GC | Meadowbrook CC |
| 2015 | Joachim GC | Quincy CC |
| 2016 | Bellerive CC | Greenbriar Hills CC |
| 2017 | Meadowbrook CC | Joachim GC |
| 2018 | Meadowbrook CC | Norwood Hills CC |
| 2019 | Meadowbrook CC | Old Hickory GC |
| 2020 | Westborough CC | The Legends CC |
| 2021 | Old Hickory GC | Spring Lake CC |
| 2022 | Quincy CC | Tapawingo National GC |