| Year | Winner | Runner Up | Venue |
| 2011 | Jamie Rutherford, Knebworth | John Ambridge, Moor Park | Moor Park Golf Club |
| 2010 | Nick Ward, Redbourn | Callum Shinkwin, Moor Park | Sandy Lodge Golf Club |
| 2009 | Nick Pateman, Porters Park | Jason Court, Sandy Lodge | Ashridge Golf Club |
| 2008 | Paul Amess, Knebworth | Chris Tingey, Mid-Herts | Knebworth Golf Club |
| 2007 | Ben Cooper, Bishops Stortford | Laurence Allen, Brookmans Park | Berkhamsted Golf Club |
| 2006 | Nick Pateman, Porters Park | Tom Shadbolt, Mid Herts | Moor Park Golf Club |
| 2005 | Tom Shadbolt, Mid-Herts | Nick Pateman, Porters Park | Letchworth Golf Club |
| 2004 | Rob Leonard, Harpenden Common | Chris Tingey, Mid Herts | Old Fold Manor Golf Club |
| 2003 | Ben Connelly, Porters Park | Tyrone Carter, Welwyn Garden City | Brookmans Park Golf Club |
| 2002 | Ben Connelly, Porters Park | | Knebworth |
| 2001 | M. Payne, Brickendon Grange | | Hadley Wood |
| 2000 | I. Farrant, Harpenden Common | | Moor Park |
| 1999 | D. Griffths, West Herts | | Porters Park |
| 1998 | R. Conway-Lye, The Hertfordshire | | South Herts |
| 1997 | C. Duke, Porters Park | | West Herts |
| 1996 | S. Little, Moor Park | | Ashridge |
| 1995 | M. Steel, Moor Park | | Moor Park |
| 1994 | G. Maly, Porters Park | | Sandy Lodge |
| 1993 | S. Burnell, Brickendon Grange | | Berkhamsted |
| 1992 | S. Burnell, Brickendon Grange | | Old Ford Manor |
| 1991 | M. Peate, Harpenden Common | | Brookmans Park |
| 1990 | N.A. Leconte, Berkhamsted | | Knebworth |
| 1989 | S. Hankin, Letchworth | | Hadley Wood |
| 1988 | J.E. Ambridge, Moor Park | | West Herts |
| 1987 | A. Clark, Old Fold Manor | | Porters Park Golf Club |
| 1986 | P.J. Cherry, Welwyn Garden City | | |
| 1985 | P.R. Robinson, Knebworth | | |
| 1984 | N.J. Briggs, Berkhamsted | | |
| 1983 | C. McKay, Letchworth | | |
| 1982 | J.E. Ambridge, Moor Park | | |
| 1981 | R.Y. Mitchell, Welwyn Garden City | | |
| 1980 | J.E. Ambridge, Moor Park | | |
| 1979 | D.F. Williams, Ashridge | | |
| 1978 | R.A. Durrant, Moor Park | | |
| 1977 | D.C. Allen, Welwyn Garden City | | |
| 1976 | R.A. Durrant, Moor Park | | |
| 1975 | N.A. Faldo, Welwyn Garden City | | |
| 1974 | R.A. Durrant, Moor Park | | |
| 1973 | H.C. Squirrell, Moor Park | | |
| 1972 | D.M. Woolmer, Ashridge | | |
| 1971 | A.W. Holmes, South Herts | | |
| 1970 | M.E. Hastings, Moor Park | | |
| 1969 | A.W. Holmes, South Herts | | |
| 1968 | P.N. Wingfield, Moor Park | | |
| 1967 | A.W. Holmes, South Herts | | |
| 1966 | D.C. Allen, Welwyn Garden City | | |
| 1965 | B.H.G. Chapman, Porters Park | | |
| 1964 | P.M. Townsend, Porters Park | | |
| 1963 | H.C. Squirrell, Moor Park | | |
| 1962 | B.H.G. Chapman, Porters Park | | |
| 1961 | S.N. Perry, Bushey Hall | | |
| 1960 | W.J. Glennie, South Herts | | |
| 1959 | G.H. Dudley, Brookmans Park | | |
| 1958 | G.A.D. Dailey, West Herts | | |
| 1957 | T.S. Waddle, Sandy Lodge | | |
| 1956 | B.H.G. Chapman, Porters Park | | |
| 1955 | E. Holt, Porters Park | | |
| 1954 | C.G. Ostler, Porters Park | | |
| 1953 | E. Holt, Porters Park | | |
| 1952 | E.R. Anscombe, Harpenden Common | | |
| 1951 | B.M. Atkinson, Bishops Stortford | | |
| 1950 | E. Holt, Oxhey Park | | |
| 1949 | G.A. Hill, Sandy Lodge | | |
| 1948 | K. Leslie Smith, Moor Park | | |
| 1947 | P.B. Lucas, Sandy Lodge | | |
| 1946 | P.B. Lucas, Sandy Lodge | | |
| 1945 | No Championship | | |
| 1944 | No Championship | | |
| 1943 | No Championship | | |
| 1942 | No Championship | | |
| 1941 | No Championship | | |
| 1940 | No Championship | | |
| 1939 | C.W. Measor, Berkhamsted | | |
| 1938 | W.R.P. Gronow, Moor Park | | |
| 1937 | M.G.S. Fox, Hartsbourne | | |
| 1936 | J. McKay, Oxhey Park | | |
| 1935 | J. McKay, Oxhey Park | | |
| 1934 | J. McKay, Oxhey Park | | |
| 1933 | J.H. Neal, Moor Park | | |
| 1932 | H.E. Rance, Berkhamsted | | |
| 1931 | R.E.A. Bott, Porters Park | | |
| 1930 | P.L.Smith, Oxhey Park | | |
| 1929 | G.G.M. Bennett, Sandy Lodge | | |
| 1928 | J.B. Anderson, Oxhey Park | | |
| 1927 | L.G. Lambourne, Moor Park | | |
| 1926 | M.R.C. Young, Sandy Lodge | | |
| 1925 | C.N. Flint, Bushey Hall | | |
| 1924 | C.N. Flint, Bushey Hall | | |
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