| Year | Course | Winner | Score | |
| 1 | 5/17/1998 | Dubbs Dread | Fore | |
| 2 | 6/13/1999 | Pine Grove | Fore | |
| 3 | 6/11/2000 | Ponderosa | Fore | |
| 4 | 7/8/2001 | Meadowink | Fore | |
| 5 | 7/28/2002 | Meadowink | Rose | |
| 6 | 7/27/2003 | Cedarbrook | Fore | |
| 7 | 7/25/2004 | Meadowink | Fore | |
| 8 | 7/17/2005 | Madison | Fore | |
| 9 | 8/20/2006 | Cedarbrook Gold | Fore | |
| 10 | 8/5/2007 | Madison | Fore | |
| 11 | 8/10/2008 | Scenic Valley | Rose | 13 to 6 |
| 12 | 8/23/2009 | Scenic Valley | Fore | 9 to 6 |
| 13 | 8/15/2010 | Cedarbrook Gold | Fore | 14 to 6 |
| 14 | 7/24/2011 | Riverview | Rose | 15 to 6 |
| 15 | 8/7/2012 | Westwood | Rose | 8 to 7 |
| 16 | 7/28/2013 | Madison | Fore | 10 to 6 |
| 17 | 8/17/2014 | Cedarbrook Gold | Fore | 9 to 8 |
| 18 | 8/30/2015 | Butlers Woodside | Rose | 11.5 to 7.5 |
| 19 | 7/31/2016 | Butlers Woodside | Rose | 11.5 to 9.5 |
| 20 | 8/30/2017 | Butlers Woodside | Fore | 11.5 to 9.5 |
| 21 | 8/19/2018 | Butlers Woodside | Fore | 12 to 10 |
| 22 | 8/11/2019 | Meadowink | Fore | 14.5 to 4 |
| 23 | 8/9/2020 | Madison | Fore | 14 to 6 |
| 24 | 8/8/2021 | Riverview | Fore | 9.5 to 8.5 |
| 25 | 8/7/2022 | Quicksilver | Rose | 17 to 5 |