| Year | Winner | Team | | Runner Up | Team |
| 2023/24 | G Redshaw & A Davis | Brewers | | C Jackson & K Jackson | Dorset A |
| 2022/23 | F Jackson & B Guilford | Dorset | | M Jordan & N Jordan | St Marys |
| 2021/22 | - | - | | - | - |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | M Hammond & S Riggs | Green Man | | S Bastone & L Bastone | Dorset B |
| 2017/18 | M Hammond & S Riggs | Green Man | | D Harding & S Harding | Tally Ho B |
| 2016/17 | A Kemp & B Guilford | Royal Oak | | P Dickens & L Smith | Green Man |
| 2015/16 | R Gillingham & S Boniface | Fountain | | D Harding & S Harding | Tally Ho B |
| 2014/15 | R Harding jnr & S Thorpe | Tally Ho B | | J Jackson & B Kemp | Royal Oak |
| 2013/14 | S Harding & D Harding | Tally Ho B | | B Guilford & A Kemp | Royal Oak |
| 2012/13 | S Harding & D Harding | Tally Ho B | | B Guilford & A Kemp | Royal Oak |
| 2011/12 | N Jordan & M Jordan | Tally Ho Wanderers | | T Hubbard & J Hubbard | Tally Ho B |
| 2010/11 | A Melrose & P Tillstone | St Marys 69ers | | N Jordan & M Jordan | Royal Oak A |
| 2009/10 | N Jordan & M Jordan | Royal Oak A | | S Thorpe & R Harding jnr | Tally Ho B |
| 2008/09 | S Harding & D Harding | Tally Ho B | | P Hughes & A Hughes | Elephant & Castle |
| 2007/08 | B Guilford & M Whiting | Pelham A | | S Harding & D Harding | Tally Ho B |
| 2006/07 | B Guilford & M Whiting | Pelham A | | S Harding & D Harding | Tally Ho B |
| 2005/06 | L Johnson & R Blay | Bridgeview | | N Hobby & M Jordan | Pelham A |
| 2004/05 | D Oakman & S Oakman | Tally Ho B | | S Harding & D Hardng | Tally Ho X |
| 2003/04 | R West & J Arnold | Tally Ho B | | | |
| 2002/03 | L Johnson & R Blay | Bridgeview | | J Powell & M Whiting | Volunteer A |
| 2001/02 | M Brett & S Bastone | Pelham A | | L Gillett & R Harding | Pelham A |
| 2000/01 | D Oakman & S Oakman | Tally Ho B | | J Gillett & D D Sains | Dorset B |
| 1999/00 | S Collard & R Harding | Tally Ho B | | S Sains & D Harding | Volunteer A |
| 1998/99 | J Gillett & R Harding | Pelham A |
| 1997/98 | S Oakman & D Oakman | Tally Ho B |
| 1996/97 | D Weller & T Carroll | Malling |
| 1995/96 | D Clayton & B Kirwood | Tally Ho A |
| 1994/95 | R Richardson & P Gates | St Marys |
| 1993/94 | H Harding & R Harding | Malling |
| 1992/93 | P Hill & T Carroll | Malling |
| 1991/92 | N Carroll & F Symes | Malling A |
| 1989/90 | I Smart & F Symes | Malling A |
| 1988/89 | N Carroll & T Carroll | Prince of Wales |
| 1987/88 | R Hopkins & D Saunders | Lansdown |
| 1986/87 | << Not Recorded >> | |
| 1985/86 | S Reed & Mrs K Hewson | Lansdown A |
| 1984/85 | D Marchant & Miss C Marchant | Lansdown A |
| 1983/84 | G Lewis & Miss A Wilby | Lansdown |
| 1982/83 | S Reed & Miss K Hewson | |
| 1981/82 | I Small & Mrs D Lee | Tally Ho |
| 1980/81 | C Walton & Miss B Lavin | Fruiterers |
| 1979/80 | D Weller & Mrs R Weller | Fruiterers |
| 1978/79 | D Weller & Mrs R Weller | Fruiterers |
| 1977/78 | D Weller & Mrs R Weller | Jolly Friars |
| 1976/77 | D Smith & Mrs J Allen | Fruiterers |
| 1975/76 | << Not Recorded >> | |
| 1974/75 | P Welch & Mrs P Welch | Lansdown |
| 1973/74 | P Welch & Mrs P Welch | Lansdown |
| 1972/73 | Mr & Mrs Kellery | Windmill |
| 1971/72 | Mr & Mrs Payne | Royal Oak |
| 1970/71 | G Windless & Mrs Windless | Chalk Pit |
| 1969/70 | P Welch & Mrs Welch | Jolly Friars |
| 1968/69 | D Smith & Mrs Allen | British Legion |
| 1967/68 | D Ottley & Mrs Johnson | Jolly Friars |
| 1966/67 | A Small & Mrs Underdown | Snowdrop |
| 1965/66 | D Smith & Mrs Allen | Bell Inn |
| 1964/65 | D Ottley & Mrs Johnson | Jolly Friars |
| 1963/64 | D Smith & Mrs Allen | Bell Inn |
| 1962/63 | D Smith & Mrs Allen | Bell Inn |
| 1961/62 | A Funnell & Mrs Pilbeam | Railway Inn |
| 1960/61 | D Ottley & Mrs Harris | Jolly Friars |
| 1959/60 | J Carter & Mrs White | Jolly Friars |
| 1958/59 | D Ottley & Mrs McLarnon | Jolly Friars |
| 1957/58 | D Smith & L Stredwick | Jolly Friars |
| 1956/57 | Mr & Mrs Hoad | Black Horse |
| 1955/56 | Mr & Mrs Milham | Royal Oak |
| 1954/55 | A Emler & Mrs McLarnon | Gardeners Arms |
| 1953/54 | Mr & Mrs Brooks | Swan Hotel |
| 1952/53 | Mr & Mrs Milham | Rifleman |
| 1951/52 | Mr & Mrs R Roser | Royal Oak |
| 1950/51 | Mr & Mrs Milham | Y Worry |
| 1949/50 | F Goldsmith & Mrs V Steer | Prince of Wales |