| Year | Winner | Runner Up | |
|---|---|---|---|
| 2023/24 | Dorset A | St Marys | |
| 2022/23 | Dorset | Green Man | |
| 2021/22 | Brewers | The Dorset | |
| 2020/21 | - | - | |
| 2019/20 | - | - | |
| 2018/19 | Green Man | Brewers | |
| 2017/18 | Green Man | Tally Ho B | |
| 2016/17 | Tally Ho B | Green Man | |
| 2015/16 | Tally Ho B | Con Club | |
| 2014/15 | Tally Ho Wanderers | Tally Ho B | |
| 2013/14 | Tally Ho Wanderers | Tally Ho B | |
| 2012/13 | Tally Ho B | Tally Ho Wanderers | |
| 2012/12 | Tally Ho B | Tally Ho Wanderers | |
| 2010/11 | Brewers | Royal Oak A | |
| 2009/10 | Brewers | Tally Ho B | |
| 2008/09 | Bridgview | Pelham A | |
| 2007/08 | Pelham A | Bridgeview & Tally Ho B | |
| 2006/07 | Tally Ho B | Pelham A | |
| 2005/06 | Pelham A | Tally Ho B | |
| 2004/05 | Tally Ho B | Tally Ho X | |
| 2003/04 | Tally Ho B | ||
| 2002/03 | Volunteer A | Pelham A | |
| 2001/02 | Volunteer A | Glynde WMC | |
| 2000/01 | Volunteer A | Tally Ho B | |
| 1999/00 | Tally Ho B | Volunteer A | |
| 1998/99 | Lamb A | ||
| 1997/98 | Pelham A | ||
| 1996/97 | Lamb A | ||
| 1995/96 | Malling | ||
| 1994/95 | Trevor Arms | ||
| 1993/94 | Trevor Arms | ||
| 1992/93 | Tally Ho | ||
| 1991/92 | Malling A | ||
| 1990/91 | Pewter Pot | ||
| 1989/90 | Pewter Pot | ||
| 1988/89 | Prince of Wales A | ||
| 1987/88 | Prince of Wales A | ||
| 1986/87 | Lansdown A | ||
| 1985/86 | Tally Ho A | ||
| 1984/85 | Lansdown A | ||
| 1983/84 | Lansdown Arms A | ||
| 1982/83 | Lansdown Arms A | ||
| 1981/82 | Fruiterers Arms B | ||
| 1980/81 | Tally Ho A | ||
| 1979/80 | Fruiterers | ||
| 1978/79 | Fruiterers | ||
| 1977/78 | Jolly Friars | ||
| 1976/77 | Fruiterers Arms C | ||
| 1975/76 | Jolly Friars | ||
| 1974/75 | Jolly Friars | ||
| 1973/74 | Not Recorded | ||
| 1972/73 | Jolly Friars | ||
| 1971/72 | Jolly Friars | ||
| 1970/71 | Jolly Friars | ||
| 1969/70 | Not Recorded | ||
| 1968/69 | Royal Oak A | ||
| 1967/68 | Jolly Friars | ||
| 1966/67 | Royal Oak | ||
| 1965/66 | Jolly Friars | ||
| 1964/65 | Royal Oak | ||
| 1963/64 | Royal Oak | ||
| 1962/63 | Royal Oak | ||
| 1961/62 | Royal Oak | ||
| 1960/61 | Royal Oak | ||
| 1959/60 | Royal Oak | ||
| 1958/59 | Jolly Friars | ||
| 1957/58 | Dorset Arms | ||
| 1956/57 | Royal Oak | ||
| 1955/56 | Royal Oak | ||
| 1954/55 | Royal Oak | ||
| 1953/54 | Royal Oak | ||
| 1952/53 | Rifleman | ||
| 1951/52 | Castle | ||
| 1950/51 | Castle | ||
| 1949/50 | Crown Shades | ||
| 1948/49 | Castle Inn | ||
| 1947/48 | Castle Inn | ||
| 1946/47 | Castle Inn | ||
| 1940-45 | Not Played | ||
| 1939/40 | Bell Inn | ||
| 1938/39 | Bell Inn | ||
| 1937/38 | Lamb Hotel | ||
| 1936/37 | Stag Hotel |
| Year | Winner | Runner Up | |
|---|---|---|---|
| 2007/08 | Seahaven Brewers | Meridian 69ers | |
| 2006/07 | Tally Ho A | LWMC | |
| 2005/06 | Elephant & Castle | LWMC | |
| 2004/05 | Black Horse | Meridian B | |
| 2003/04 | Tally Ho A | ||
| 2002/03 | Dorset Arms | Tally Ho A | |
| 2001/02 | St Marys | Meridian B | |
| 2000/01 | Pelham B | Dorset Arms | |
| 1999/00 | Pewter Pot | Swan B |