Each year the past captains of the society challenge the committee and organisers. Details of the current year's format are on the Challenge Matches page.
| Year | Winner |
Score | Course |
| 2011 | Captain | 7.5 - 5.5 | Royal Winchester |
| 2010 | President | 9.5 - 8.5 | Royal Winchester |
| 2009 | Captain | 8 - 7 | Royal Winchester |
| 2008 | Captain | 7 - 5 | Royal Winchester |
| 2007 | Captain | 11 - 4 | Royal Winchester |
| 2006 | Captain | Royal Winchester | |
| 2005 | Draw | Royal Winchester | |
| 2004 | Captain | Royal Winchester | |
| 2003 | President | Royal Winchester | |
| 2002 | Captain | Royal Winchester | |
| 2001 | Draw | Royal Winchester | |
| 2000 | Captain | Royal Winchester |