The Riddell Challenge Cup is the Society’s oldest trophy. It was presented by George Riddell in 1905 and was originally played as a handicap matchplay event (sometimes with a 36 hole final) after initial qualification at the Summer Meeting. It is now awarded as a handicap prize at the Spring Meeting for Society members aged 50 or over.
| Year | Winner |
|---|---|
| 1905 | J. Hall |
| 1906 | H. Mossop |
| 1907 | H. Mossop |
| 1908 | H.W. Patey |
| 1909 | F. Carver |
| 1910 | J. Hall |
| 1911 | A.J. Lamb |
| 1912 | E. Glenshaw |
| 1913 | H.B.W. Foulger |
| 1914 | J. Woodhouse |
| 1915 – 18 | War |
| 1919 | T. Rothwell Haslam |
| 1920 | B. Trayton Kenward |
| 1921 | E.S. Trehearne |
| 1922 | B. Trayton Kenward |
| 1923 | Arnold Carter |
| 1924 | B. Trayton Kenward |
| 1925 | C.H. Hornby |
| 1926 | Sydney Newman |
| 1927 | D. Williams |
| 1928 | F. Fernihough |
| 1929 | R.W. Ripley |
| 1930 | C.F. Rowlands |
| 1931 | C.R. Steele |
| 1932 | K.M. Beaumont |
| 1933 | E.H. Coe |
| 1934 | R.C. Bolton |
| 1935 | E.H. Coe |
| 1936 | B.M. Patey |
| 1937 | Sam Cook |
| 1938 | J.L. De La Cour |
| 1939-48 | No Competition |
| 1949 | D.I.C. Cooke |
| 1950 | T.E.P. Martin |
| 1951 | L.G.D. Loft |
| 1952 | H.W. Meaby |
| 1953 | No record |
| 1954 | J.D. Haslam |
| 1955 | F.G. Petch |
| 1956 | R. Woolf |
| 1957 | H.F. Bathurst Brown |
| 1958 | L.G.D. Loft and R. Woolf |
| 1959 | H.W. Meaby |
| 1960 | E.A.S. Brooks |
| 1961 | P.M. Armitage |
| 1962 | D.O. Smith |
| 1963 | G.P.O’N. Pearson |
| 1964 | D.O. Smith |
| 1965 | D.H. Haslam |
| 1966 | J.R.E. Drooglever |
| 1967 | J. Chambres |
| 1968 | J.D. Watney |
| 1969 | G.P.O’N. Pearson |
| 1970 | H.C.E. Johnson |
| 1971 | Hidden by Henry Johnson |
| 1972 | |
| 1973 | |
| 1974 | T.F.P. Martin |
| 1975-6 | Not Awarded |
| 1977 | J.R.N. Holdsworth |
| 1978 | T.F.P. Martin |
| 1979 | J. Geils |
| 1980 | H.S. Maxwell-Wood |
| 1981 | F.M. Emmett |
| 1982 | F.A. Barnsdale |
| 1983 | P.M. Davies |
| 1984 | J. Geils |
| 1985 | P.J. Morley-Jacob |
| 1986 | R.F. Gardner |
| 1987 | E.A.S. Brooks |
| 1988 | C. Clogg |
| 1989 | F.A. Barnsdale |
| 1990 | Anthony Surtees |
| 1991 | Andrew Gerry |
| 1992 | Bill Farrer |
| 1993 | Arfon Jones |
| 1994 | Jeremy Caplan |
| 1995 | Clive Rumbelow |
| 1996 | Adrian Watney |
| 1997 | Martyn Gowar |
| 1998 | Peter Morley-Jacob |
| 1999 | David Wyld |
| 2000 | Anthony Surtees |
| 2001 | Hugh Elder |
| 2002 | David Wright |
| 2003 | Andrew Daws |
| 2004 | Harry Anderson |
| 2005 | Christopher Johnson-Gilbert |
| 2006 | Brian Meaby |
| 2007 | Ian Elder |
| 2008 | Peter Hewes |
| 2009 | Brian Meaby |
| 2010 | Brian Meaby |