| Year | Winner | Team | | Runner Up | Team |
| 2021/22 | - | - | | - | - |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | G Redshaw & M Houkes jnr | Brewers | | S Jackson & F Jackson | Dorset A |
| 2017/18 | S Jackson & F Jackson | Dorset | | G Redshaw & M Houkes jnr | Brewers |
| 2016/17 | D Welfare & D Trott | Green Man | | A Kemp & J Jackson | Royal Oak |
| 2015/16 | J Whiting & M Whiting | Con Club | | G Redshaw & K Dartnell | Brewers |
| 2014/15 | J Whiting & M Whiting | Con Club | | S Kemp & R Harding jnr | Tally Ho B |
| 2013/14 | S Bastone & D D Sains | Tally Ho Wanderers | | A Kemp & J Jackson | Royal Oak |
| 2012/13 | R Blay & B Johnson | Brewers | | A Kemp & J Jackson | Royal Oak |
| 2011/12 | J Whiting & M Whiting | Con Club | | R Harding jnr & D Harding | Tally Ho B |
| 2010/11 | R Harding jnr & D Harding | Tally Ho B | | R Blay & B Johnson | Brewers |
| 2009/10 | R Harding jnr & D Harding | Tally Ho B | | G Houkes & J Harland | Elephant & Castle |
| 2008/09 | R Harding jnr & R Harding | Tally Ho B | | S Tillstone & P Telford | Meridian 69ers |
| 2007/08 | R Blay & B Johnson | Bridgeview | | C Whiting & K Phillips | Elly Old Nags |
| 2006/07 | S Bastone & M Jordan | Pelham A | | G Laker & D Inman | Meridian A |
| 2005/06 | S Bastone & M Jordan | Pelham A | | R Harding jnr & S Oakman | Tally Ho B |
| 2004/05 | M Earl & S Oakman | Tally Ho B | | B Jordan & T Kemp | Meridian B |
| 2003/04 | S Bastone & D Weller | Pelham A | | | |
| 2002/03 | S Bastone & R Gillett | Pelham A | | E Chapman & K Dartnell | Swan |
| 2001/02 | W Cook & D Harding | Volunteer A | | S Bastone & R Gillett | Pelham A |
| 2000/01 | J Cook & A Kemp | Pelham B | | B Johnson & R Chappell | Bridgeview |
| 1999/00 | G Redshaw & N Carroll | Malling | | J Brown & S Jarvis | Black Horse |