Under 25s
| Year | Winner | Team | | Runner Up | Team |
| 2021/22 | F Jackson | The Dorset | | H Jackson | The Dorset |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | R Rodford | Tally Ho B | | F Jackson | Dorset A |
| 2017/18 | B Gardner | Con Club | | R Rodford | Tally Ho B |
| 2016/17 | H Jackson | Royal Oak | | B Gardner | Con Club |
| 2015/16 | J Whiting | Con Club | | J Jackson | Royal Oak |
| 2014/15 | J Whiting | Con Club | | S Telford | Tally Ho B |
| 2013/14 | J Jackson | Royal Oak | | R Rodford | Tally Ho B |
| 2012/13 | C Williams | Anchor | | S Telford | Tally Ho B |
| 2011/12 | B Gardner | Con Club | | J Jackson | Royal Oak |
| 2010/11 | B Gardner | Con Club | | J Whiting | Con Club |
| 2009/10 | J Scott | Royal Oak B | | D Crowhurst | Brewers |
| 2008/09 | S Barnard | Bridgeview | | D Martin | Pelham A |
| 2007/08 | A Davis | Bridgeview | | S Kemp | Meridian A |
| 2006/07 | M Hammond | Swan | | K Small | Meridian 69ers |
| 2005/06 | A Davis | Brdiegview | | D Martin | St Marys |
| 2004/05 | A Davis | Bridgeview | | R Knight | Elephant & Castle |
| 2003/04 | A Davis | Bridgeview | | | |
| 2002/03 | A Davis | Bridgeview | | L Wheeler | Tally Ho |
| 2001/02 | A Davis | Glynde WMC | | R Knight | Glynde WMC |
| 2000/01 | A Davis | Trevor Arms | | A Harman | Pewter Pot |
| 1999/00 | S Bastone | Meridian A | | M Pomfrey | Malling |
| 1998/99 | D Woolgar | Lamb A |
| 1997/98 | R F Harding | Pelham A |
| 1996/97 | D Sains | Malling |
| 1995/96 | G Redshaw | Malling |
| 1994/95 | D Fyffe | Pewter Pot B |
| 1993/94 | D N Sains | Tally Ho |
| 1992/93 | D N Sains | Tally Ho |
| 1991/92 | not recorded | not recorded |
| 1990/91 | D N Sains | Swan |
| 1989/90 | G Swain | Malling Exiles |
| 1988/89 | G Turner | Top Legion |