| Season | Winner | Runner-up | Note(s) |
|---|---|---|---|
| 1883-84 | Croydon | South Norwood | Originally called the Surrey Club Trophy Challenge Cup: Herbert Jacobs Croydon |
| 1884-85 | Brixton | South Norwood | Challenge Cup: Daniel Y. Mills South Norwood |
| 1885-86 | Brixton | South Norwood | Brixton won on games points scored Challenge Cup: Wyke Bayliss Brixton |
| 1886-87 | Brixton | New Cross | Challenge Cup: Herbert Jacobs Brixton |
| 1887-88 | Brixton | South Norwood | Challenge Cup: Herbert Jacobs Brixton |
| 1888-89 | Brixton | New Cross | Challenge Cup: Herbert Jacobs Brixton |
| 1889-90 | New Cross | Brixton / South Norwood | Challenge Cup: H. Swinburn Ward Brixton |
| 1890-91 | South Norwood | New Cross | Challenge Cup: William N. Osborne Brixton |
| 1891-92 | South Norwood | New Cross | Challenge Cup: J. Percy Mollard South Norwood |
| 1892-93 | South Norwood | New Cross | Challenge Cup: J. Percy Mollard South Norwood |
| 1893-94 | South Norwood | Battersea | South Norwood beat Battersea in play-off 7½-4½ Challenge Cup: Evan Creswell Battersea |
| 1894-95 | Battersea | ||
| 1895-96 | Brixton | ||
| 1896-97 | Dulwich | ||
| 1897-98 | Brixton | ||
| 1898-99 | Brixton | ||
| 1899-00 | Battersea | ||
| 1900-01 | Battersea | ||
| 1901-02 | Battersea | ||
| 1902-03 | Nightingale Lane | ||
| 1903-04 | Battersea | ||
| 1904-05 | Battersea | ||
| 1905-06 | Clapham | ||
| 1906-07 | Clapham | ||
| 1907-08 | Clapham | ||
| 1908-09 | Surbiton | ||
| 1909-10 | Brixton | ||
| 1910-11 | Clapham | ||
| 1911-12 | South Norwood | ||
| 1912-13 | South Norwood | ||
| 1913-14 | Kennington | ||
| 1914-15 | Putney | ||
| 1915-16 | Battersea | ||
| 1919-20 | Brixton | ||
| 1920-21 | Brixton | ||
| 1921-22 | Brixton | ||
| 1922-23 | Brixton | ||
| 1923-24 | Brixton | ||
| 1924-25 | Thames Valley | ||
| 1925-26 | Battersea | ||
| 1926-27 | Battersea | ||
| 1927-28 | Battersea | ||
| 1928-29 | Battersea | ||
| 1929-30 | Brixton | ||
| 1930-31 | Battersea | ||
| 1931-32 | Kingston | ||
| 1932-33 | Battersea | ||
| 1933-34 | Battersea | ||
| 1934-35 | Battersea | ||
| 1935-36 | Clapham Common | ||
| 1936-37 | Clapham Common | ||
| 1937-38 | Clapham Common | ||
| 1938-39 | Battersea | ||
| 1945-46 | Croydon | ||
| 1946-47 | Croydon | ||
| 1947-48 | Croydon | ||
| 1948-49 | Battersea | ||
| 1949-50 | Clapham Common | ||
| 1950-51 | Sutton | ||
| 1951-52 | Battersea | ||
| 1952-53 | Sutton | ||
| 1953-54 | Sutton | ||
| 1954-55 | Battersea | ||
| 1955-56 | Wimbledon | ||
| 1956-57 | Sutton | ||
| 1957-58 | Richmond | ||
| 1958-59 | Sutton | ||
| 1959-60 | Sutton | ||
| 1960-61 | Sutton | ||
| 1961-62 | Richmond | ||
| 1962-63 | Croydon | ||
| 1963-64 | Mushrooms | ||
| 1964-65 | Mushrooms | ||
| 1965-66 | Richmond | ||
| 1966-67 | Mushrooms and Richmond | Joint | |
| 1967-68 | Sutton | ||
| 1968-69 | Richmond | ||
| 1969-70 | Mitcham | ||
| 1970-71 | Mitcham | ||
| 1971-72 | Mushrooms | ||
| 1972-73 | Richmond | ||
| 1973-74 | Sutton | ||
| 1974-75 | Kingston | ||
| 1975-76 | Streatham | ||
| 1976-77 | Streatham 2 | ||
| 1977-78 | Streatham | ||
| 1978-79 | Streatham 2 | ||
| 1979-80 | Streatham | ||
| 1980-81 | Wimbledon | ||
| 1981-82 | Streatham | ||
| 1982-83 | Streatham | ||
| 1983-84 | Mitcham | ||
| 1984-85 | Guildford | ||
| 1985-86 | Streatham | ||
| 1986-87 | Mitcham | ||
| 1987-88 | Mitcham | ||
| 1988-89 | Sutton | ||
| 1989-90 | Mitcham | ||
| 1990-91 | Wimbledon | ||
| 1991-92 | Mitcham | ||
| 1992-93 | Mitcham | ||
| 1993-94 | Guildford | ||
| 1994-95 | Guildford | ||
| 1995-96 | Guildford | ||
| 1996-97 | Mitcham | ||
| 1997-98 | Coulsdon | ||
| 1998-99 | Coulsdon | ||
| 1999-00 | Coulsdon | ||
| 2000-01 | Coulsdon | ||
| 2001-02 | Coulsdon | ||
| 2002-03 | Redhill | ||
| 2003-04 | Guildford | ||
| 2004-05 | Guildford | ||
| 2005-06 | Coulsdon 1 | ||
| 2006-07 | Wimbledon 1 | ||
| 2007-08 | Redhill 1 | ||
| 2008-09 | Redhill 1 | ||
| 2009-10 | Redhill 1 | ||
| 2010-11 | Redhill 1 | ||
| 2011-12 | Redhill 1 | ||
| 2012-13 | Guildford 1 | ||
| 2013-14 | Redhill 1 | ||
| 2014-15 | CCF 1 | ||
| 2015-16 | Guildford 1 | ||
| 2016-17 | Wimbledon 1 | ||
| 2017-18 | Wimbledon 1 | ||
| 2018-19 | Surbiton 1 | ||
| 2019-20 | Guildford 1 | ||
| 2021-22 | Guilford 1 | ||
| 2022-23 | Kingston 1 | ||
| 2023-24 | Epsom 1 | ||
| 2024-25 | Kingston 1 | ||
| 2025-26 | Kingston 1 | Guildford 1 |