| Year | Club | Format | Winner 1 |
|---|---|---|---|
| 2023 | Enfield | Singles | MR Pritchett |
| 2022 | Enfield | Singles | LA Yoxall |
| 2021 | Enfield | Singles | GI Amoils |
| 2020 | Enfield | Singles | MJ Bentley |
| 2019 | Enfield | Singles | AR Eyland |
| 2018 | Enfield | Singles | O Smart |
| 2017 | Enfield | Singles | M Peak |
| 2016 | Enfield | Singles | PM Ives |
| 2015 | Enfield | Singles | K Storey |
| 2014 | Enfield | Singles | F Noto |
| 2013 | Enfield | Singles | P Carter |
| 2012 | Enfield | Singles | M Dennis |
| 2011 | Enfield | Singles | FJ Lees |
| 2010 | Enfield | Singles | DS Cassidy |
| 2009 | Enfield | Singles | S Appleton |
| 2008 | Enfield | Singles | BM Cooper |
| 2007 | Enfield | Singles | PJ Malde |
| 2006 | Enfield | Singles | PC Millard |
| 2005 | Enfield | Singles | SS Waters |
| 2004 | Enfield | Singles | AD Draper |
| 2003 | Enfield | Singles | LE Power |
| 2002 | Enfield | Singles | P Stavri |
| 2001 | Enfield | Singles | JW Dixon |
| 2000 | Enfield | Singles | WB Offord |
| 1999 | Enfield | Singles | JW Codling |
| 1998 | Enfield | Singles | TJ White |
| 1997 | Enfield | Singles | A Monk |
| 1996 | Enfield | Singles | PA Edwards |
| 1995 | Enfield | Singles | JDC Hoarton |
| 1994 | Enfield | Singles | A Hendry |
| 1993 | Enfield | Singles | M Banning |
| 1992 | Enfield | Singles | SI Warren |
| 1991 | Enfield | Singles | S Mangan |
| 1990 | Enfield | Singles | C Chapman |
| 1989 | Enfield | Singles | TW Parker |
| 1988 | Enfield | Singles | PR Millard |
| 1987 | Enfield | Singles | MJ Deal |
| 1986 | Enfield | Singles | SE Brett |
| 1985 | Enfield | Singles | TJ White |
| 1984 | Enfield | Singles | B Booth |
| 1983 | Enfield | Singles | R Greening |
| 1982 | Enfield | Singles | AR Hubbard |
| 1981 | Enfield | Singles | MTH Thurlow |
| 1980 | Enfield | Singles | WG Hulks |
| 1979 | Enfield | Singles | H Fry |
| 1978 | Enfield | Singles | PH Fisk |
| 1977 | Enfield | Singles | JG Pritchett |
| 1976 | Enfield | Singles | AJ Barnett |
| 1975 | Enfield | Singles | PJ Cunningham |
| 1974 | Enfield | Singles | WG Hulks |
| 1973 | Enfield | Singles | CG Lower |
| 1972 | Enfield | Singles | MA Neill |
| 1971 | Enfield | Singles | I Shearer |
| 1970 | Enfield | Singles | NA Challis |
| 1969 | Enfield | Singles | TE Dalzell |
| 1968 | Enfield | Singles | DS Perry |
| 1967 | Enfield | Singles | NR Field |
| 1966 | Enfield | Singles | DP Stockton |
| 1965 | Enfield | Singles | D Judd |
| 1964 | Enfield | Singles | PC Millard |
| 1963 | Enfield | Singles | JB Knight |
| 1962 | Enfield | Singles | JB Knight |
| 1961 | Enfield | Singles | DGW Norey |
| 1960 | Enfield | Singles | ES Saunders |
| 1959 | Enfield | Singles | AG Stanmore |
| 1958 | Enfield | Singles | PC Millard |
| 1957 | Enfield | Singles | RG Beck |
| 1956 | Enfield | Singles | TA Fay |
| 1955 | Enfield | Singles | LH Newstead |
| 1954 | Enfield | Singles | PR Batchelor |
| 1953 | Enfield | Singles | A Newbery |
| 1952 | Enfield | Singles | RJ Fletcher |
| 1951 | Enfield | Singles | HS Whittaker |
| 1950 | Enfield | Singles | CE Potter |
| 1949 | Enfield | Singles | RB Green |
| 1948 | Enfield | Singles | P Townsend |
| 1947 | Enfield | Singles | FA Vincent |
| 1946 | Enfield | Singles | DWP Gibbs |
| 1945 | Enfield | Singles | DSC Simmonds |
| 1940 | Enfield | Singles | NL Foster |
| 1939 | Enfield | Singles | AG Cobden |
| 1938 | Orsett | Singles | AG Atkinson |
| 1937 | Enfield | Singles | DG Piggott |
| 1936 | Enfield | Singles | AG Cobden |
| 1935 | Enfield | Singles | FW Keene |
| 1934 | Enfield | Singles | RB Lauriston |
| 1933 | Crews Hill | Singles | NE Benjafield |
| 1932 | Mote Mount | Singles | EA Hetherington |
| 1931 | Enfield | Singles | GF Gowland |
| 1930 | Enfield | Singles | AB Sendall |
| 1929 | Enfield | Singles | HF Potter |
| 1928 | Welwyn Garden City | Singles | FE Stratford |
| 1927 | Enfield | Singles | E Johns |
| 1926 | Enfield | Singles | E Potter |
| 1925 | Enfield | Singles | GJ Hogg |
| 1924 | Sidcup | Singles | FAM Luker |
| 1923 | Enfield | Singles | AT Winter |
| 1922 | Enfield | Singles | JH Thornton |
| 1921 | Gooden Beach | Singles | FG Plummer |
| 1920 | Enfield | Singles | DAW Nicholson |
| 1919 | Enfield | Singles | DAW Nicholson |
