| Year | Winner | Team | | Runner Up | Team |
| 2023/24 | D D Sains & L Sains | Dorset B | | C Thomas & S Thomas | Dorset B |
| 2022/23 | J Houkes & A Watts | Brewers | | S Turner & J Hubbard | Tally Ho B |
| 2021/22 | F Jackson & C Jackson | The Dorset | | A Davis & G Redshaw | Brewers |
| 2020/21 | - | - | | - | - |
| 2019/20 | - | - | | - | - |
| 2018/19 | M Whiting & J Whiting | Black Horse | | S Smith & W Freer | Green Man |
| 2017/18 | P Dickens & M Hammond | Green Man | | D N Sains & D Harding | Tally Ho B |
| 2016/17 | P Dickens & M Hammond | Green Man | | S Bastone & D D Sains | Royal Oak |
| 2015/16 | R Harding jnr & J Pelling | Tally Ho B | | R Gillingham & S Boniface | Fountain |
| 2014/15 | S Smith & M Jordan | Tally Ho Wanderers | | S Oakman & S Jackson | Tally Ho Wanderers |
| 2013/14 | M Jordan & S Smith | Tally Ho Wanderers | | S Bastone & D D Sains | Tally Ho Wanderers |
| 2012/13 | R Harding jnr & P Telford | Tally Ho B | | M Jordan & S Jackson | Tally Ho Wanderers |
| 2011/12 | R Harding jnr & P Telford | Tally Ho B | | D Inman & M Cornford | Tally Ho Wanderers |
| 2010/11 | R Blay & D Crowhurst | Brewers | | S Bastone & D D Sains | Royal Oak A |
| 2009/10 | S Bastone & D D Sains | Royal Oak A | | R Harding jnr & P Telford | Tally Ho B |
| 2008/09 | G Redshaw & L Griffin | Bridgeview | | P Dickens & A Cox | Pelham A |
| 2007/08 | D Harding & D N Sains | Tally Ho B | | R Harding & R Harding jnr | Tally Ho B |
| 2006/07 | M Whiting & S Jackson | Pelham A | | A Davis & S Reed | Bridgeview |
| 2005/06 | R Harding jnr & R Harding | Tally Ho B | | A Davis & R Blay | Bridgeview |
| 2004/05 | D N Sains & D Harding | Tally Ho B | | R Harding jnr & G Turner | Tally Ho B |
| 2003/04 | M Whiting & G White | Tally Ho X | | | |
| 2002/03 | D Weller & P Dickens | Pelham A | | G Redshaw & D Marchant | Dorset Arms |
| 2001/02 | C Whiting & M Jordan | Black Horse | | J Cook & J I Cook | Pelham B |
| 2000/01 | J Arnold & S Oakman | Tally Ho B | | D Harding & D N Sains | Volunteer A |
| 1999/00 | S Oakman & J Arnold | Tally Ho B | | M Whiting & G White | Volunteer A |
| 1998/99 | P Tomsett & L Ripley | Tally Ho A |
| 1997/98 | R Harding & D Wheller | Pelham A |
| 1996/97 | D Harding & D N Sains | Lamb A |
| 1995/96 | M Whiting & G White | Lamb |
| 1994/95 | D Sains & D Harding | Pelham |
| 1993/94 | R Tourle & R Williams | Swan Associates |
| 1992/93 | R Gay & A Gay | Tally Ho |
| 1991/92 | R Gay & A Gay | Tally Ho |
| 1990/91 | S Reed & G Lewis | Pewter Pot |
| 1989/90 | S Reed & G Lewis | Pewter Pot |
| 1988/89 | R Hammond & A Fielding | Prince of Wales |
| 1987/88 | R Hammond & D Leach | St Marys C |
| 1986/87 | G Lewis & S Reed | Lansdown A |
| 1985/86 | R Hammond & K Hewson | Lansdown A |
| 1984/85 | D Wheller & D Hill | LWMC |
| 1983/84 | L Ripley & J Maxwell | Prince of Wales |
| 1982/83 | D Merry & M Mason | Lansdown |
| 1981/82 | D Merry & M Mason | Fruiterers Arms |
| 1980/81 | C Walton & C Page | Fruiterers Arms |
| 1979/80 | M Moody & P Welch | Fruiterers Arms |
| 1978/79 | D Ottley & P Harris | Jolly Friars |
| 1977/78 | C Page & S Halsey | Fruiterers Arms |
| 1976/77 | L Kemp & A Hufflett | Jolly Friars |
| 1975/76 | P Welch & R Small | Tally Ho |
| 1974/75 | D Ottley & R Harris | Jolly Friars |
| 1973/74 | J Lennard & B Bodle | Jolly Friars |
| 1972/73 | A Hufflett & M Davis | Jolly Friars |
| 1971/72 | D Smith & R Roser | British Legion |
| 1970/71 | D Smith & R Roser | British Legion |
| 1969/70 | D Smith & R Roser | British Legion |
| 1968/69 | A Thompson & J Kerry | Bell |
| 1967/68 | R Roser & D Smith | British Legion |
| 1966/67 | W Milham & B Bolton | Royal Oak |
| 1965/66 | W Milham & B Bolton | Royal Oak |
| 1964/65 | R Roser & D Smith | Royal Oak |
| 1963/64 | D Nichols & A Small | Wheatsheaf |
| 1962/63 | S Bristow & J Cole | Royal Oak |
| 1961/62 | S Pilbeam & T Smith | Railway Inn |
| 1960/61 | G Harris & I Henty | Jolly Friars |
| 1959/60 | D Ottley & R Harris | Jolly Friars |
| 1958/59 | W Milham & T Lee | Royal Oak |
| 1957/58 | W Milham & T Lee | Royal Oak |
| 1956/57 | D Ottley & D Ayling | Phoenix Sports |
| 1955/56 | W Milham & T Lee | Royal Oak |
| 1954/55 | W Milham & D Sanders | Royal Oak |
| 1953/54 | S Bristow & J Cole | Royal Oak |
| 1952/53 | S Bristow & J Cole | Royal Oak |
| 1951/52 | S Bristow & J Cole | Royal Oak |
| 1950/51 | A Embler & C Thorpe | Castle |
| 1949/50 | AB Funnell & W Payne | Black Horse |
| 1948/49 | J Lamper & E Mabbott | Prince of Wales |
| 1947/48 | F Mitchell & G Mitchell | Crown Shades |
| 1946/47 | R Robins & D Saunders | Thatched House |
| 1941 - 1945 | << Not Recorded >> | |
| 1939/40 | T Lee & E Bishop | Bell Inn |