Jubilee Cup
| Year | Winners | | Runners Up |
| 2024/25 | Brewers | | Dorset B |
| 2023/24 | Brewers | | St Marys |
| 2022/23 | Brewers | | St Marys |
| 2021/22 | Brewers | | Dorset |
| 2020/21 | - | | - |
| 2019/20 | - | | - |
| 2018/19 | Brewers | | Green Man |
| 2017/18 | Green Man | | St Marys |
| 2016/17 | Royal Oak | | Brewers |
| 2015/16 | Tally Ho B | | Con Club |
| 2014/15 | Tally Ho B | | Tally Ho Wanderers |
| 2013/14 | Tally Ho Wanderers | | St Marys |
| 2012/13 | Brewers | | Tally Ho B |
| 2012/12 | Tally Ho B | | Tally Ho Wanderers |
| 2010/11 | Brewers | | Con Club |
| 2009/10 | Tally Ho A | | Royal Oak A |
| 2008/09 | Pelham A | | Bridgeview |
| 2007/08 | Bridgeview | | Pelham A |
| 2006/07 | Pelham A | | Bridgeview |
| 2005/06 | Tally Ho B | | Pelham A |
| 2004/05 | Tally Ho X | | Tally Ho A |
| 2003/04 | Bridgeview | | |
| 2002/03 | Tally Ho B | | Pelham A |
| 2001/02 | Volunteer | | Pelham A |
| 2000/01 | Volunteer | | Trevor Arms |
| 1999/00 | Tally Ho B | | Tally Ho A |
| 1998/99 | Tally Ho A |
| 1997/98 | Tally Ho A |
| 1996/97 | Lamb |
| 1995/96 | Lamb |
| 1994/95 | Pelham |
| 1993/94 | Malling |
| 1992/93 | Trevor Arms |
| 1991/92 | Tally Ho |
| 1990/91 | Pewter Pot |
| 1989/90 | Malling |
| 1988/89 | Prince of Wales |
| 1987/88 | St Marys C |
| 1986/87 | Lansdown A |