Mens Singles
| Year | Winner | Team | | Runner Up | Team |
| 2024/25 | A Davis | Brewers | | C Thomas | Dorset B |
| 2023/24 | L Sains | Dorset B | | A Davis | Brewers |
| 2022/23 | B Payne | Green Man | | M Whiting | St Marys |
| 2021/22 | D D Sains | The Dorset | | A Davis | Brewers |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | M Hammond | Green Man | | H Jackson | Dorset A |
| 2017/18 | D Harding | Tally Ho B | | B Gardner | Con Club |
| 2016/17 | H Jackson | Royal Oak | | M Whiting | Con Club |
| 2015/16 | G Redshaw | Brewers | | M Whiting | Con Club |
| 2014/15 | P Telford | Tally Ho B | | R Gillingham | Fountain |
| 2013/14 | P Telford | Tally Ho B | | D D Sains | Tally Ho Wanderers |
| 2012/13 | J Jackson | Royal Oak | | J Barnes | St Mary's |
| 2011/12 | R Blay | Brewers | | D D Sains | Tally Ho Wanderers |
| 2010/11 | M Whiting | Con Club | | P Telford | Tally Ho B |
| 2009/10 | D Harding | Tally Ho B | | M Jordan | Royal Oak A |
| 2008/09 | S Bastone | Pelham A | | A Davis | Bridgeview |
| 2007/08 | P Telford | Meridian 69ers | | M Jordan | Pelham A |