Thomas O. Sobbe Cup Champions
| Year | Champion | Champion Points | Runner-Up Points | 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* | 3* | 3 | Joachim GC |
| 2018 | Meadowbrook CC | 3.5 | 2.5 | Norwood Hills CC |
| 2019 | Meadowbrook CC* | 3* | 3 | Old Hickory GC |
| 2020 | Westborough CC* | 3* | 3 | The Legends CC |
| 2021 | Old Hickory GC | 4 | 2 | Spring Lake CC |
| 2022 | Quincy CC* | 3* | 3 | Tapawingo National GC |
| 2023 | Glen Echo CC | 4 | 2 | Bogey Hills CC |
*Won in a playoff