Qualifying for the winter cup is run on the first three weeks after the pennants season The top eight members qualify for the three rounds of Match Play.
From 2024 the 2 Players who make the final will receive a free round of golf as a prize.
| Year | Winner | Year | Winner | Year | Winner |
| 1986 | E. McNally | 1987 | R. Charles | 1988 | Pat Pereira |
| 1989 | David Smith | 1990 | Bluey Smith | 1991 | Jack Ebbs |
| 1992 | K. Norman | 1993 | Pat Pereira | 1994 | Shane Kahler |
| 1995 | Shane Kahler | 1996 | George Crawford | 1997 | Andrew Dallinger |
| 1998 | Kim Pelham | 1999 | Peter Butler | 2000 | Tom Meiklejohn |
| 2001 | David Wade | 2002 | Vic Worobec | 2003 | Terry Nind |
| 2004 | Chris Gifford | 2005 | Greg Mackintosh | 2006 | Alun Wyn-Jones |
| 2007 | Greg Kelly | 2008 | Alun Wyn-Jones | 2009 | Steve Roberts |
| 2010 | Dave Firstenberg | 2011 | Mike Bunyan | 2012 | Wayne Peppernell |
| 2013 | Kevin Fairhead | 2014 | Tyson LeBrun | 2015 | Dan Kilderry |
| 2016 | Craig Thompson | 2017 | Alan Godfrey | 2018 | Colin Boyle |
| 2019 | Eric Lavelle | 2020 | Derek Gibson | 2021 | Piers Higham |
| 2022 | John Simonetti | 2023 | Mark Winsor |