Over 50s
| Year | Winner | Team | | Runner Up | Team |
| 2021/22 | G Redshaw | Brewers | | P Tillstone | Brewers |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | M Whiting | Black Horse | | E Chapman | Tally Ho A |
| 2017/18 | M Whiting | Con Club | | P Tillstone | Brewers |
| 2016/17 | M Whiting | Con Club | | M Jordan | Royal Oak |
| 2015/16 | M Jordan | Con Club | | P Martin | Fountain |
| 2014/15 | S Geer | St Marys | | D Welfare | Green Man |
| 2013/14 | B Sains | Tally Ho A | | D Welfare | Green Man |
| 2012/13 | G Day | St Marys | | D Trott | Tally Ho Wanderers |
| 2011/12 | J Barnes | St Marys | | D Marchant | Tally Ho Wanderers |
| 2010/11 | R Chappell | New Lewes Workers | | M Packham | Con Club |
| 2009/10 | D Grindon | Tally Ho B | | D Champion | LWMC |
| 2008/09 | K Dartnell | Swan | | R Chapell | Bridgeview Stags |
| 2007/08 | D Grindon | Tally Ho B | | D Champion | LWMC |
| 2006/07 | D Marchant | Pelham A | | B Wheeler | Tally Ho B |
| 2005/06 | D Marchant | Pelham A | | D Arnold | Swan |
| 2004/05 | D Marchant | Pelham A | | K Dartnell | Swan |
| 2003/04 | D Grindon | Tally Ho B | | | |
| 2002/03 | D Weller | Pelham A | | A Cox | Pelham A |
| 2001/02 | D Champion | LWMC | | S Small | Tally Ho A |
| 2000/01 | R Chappell | Bridgeview | | K Callister | Pewter Pot |
| 1999/00 | E Pilbeam | Trevor Arms | | K Phillips | Black Horse |