In the early years of the club, the Caines Cup was awarded to the winner of an all-play-all club championship competition run throughout the season. There was also a separate 5 round Swiss tournament (usually 1 game per month) which players also competed for with the winner receiving the Cheeseman Trophy.
In more recent times when the Swiss tournament was discontinued, this was changed so that the winner of the all-play-all Club Championship received the Cheeseman Trophy with the runner up being awarded the Caines Cup.
In 2018, the club championship was split into two sections: an Open section for all members and a Major section for players rated under 1825.
The winner of the Open section receives the Cheeseman Trophy and the winner of the Major section receives the Caines Cup.
| 2024 | TBD |
| 2023 | Paul Hampton |
| 2022 | Paul Hampton |
| 2020 | Paul Hampton |
| 2019 | Jon Underwood |
| 2018 | Paul Hampton |
| 2017 | Alan Dowse |
| 2016 | Steve Dean |
| 2015 | Steve Dean |
| 2014 | Steve Dean |
| 2013 | Steve Dean |
| 2012 | Steve Dean |
| 2011 | Alan Dowse |
| 2010 | M. Adams |
| 2009 | Steve Dean |
| 2008 | Hazel Welch |
| 2007 | Steve Dean |
| 2006 | Steve Dean |
| 2005 | Robert Ryan |
| 2004 | Hazel Welch |
| 2003 | Jon Underwood |
| 2002 | Les Porter |
| 2001 | R. A. Ryan |
| 2000 | Paul Rogers |
| 1999 | Paul Rogers |
| 1998 | Paul Rogers |
| 1997 | P. Rogers & G. Snell |
| 1996 | Paul Rogers |
| 1995 | Paul Rogers |
| 1994 | Paul Rogers |
| 1993 | Jim O'Grady & Martin Nex |
| 1992 | Paul Rogers |
| 1991 | Paul Rogers |
| 1990 | Jim O'Grady |
| 1989 | Jim O'Grady |