Winners of Challenge Cup
Challenge Cup. First presented in 1929. Men's Singles Matchplay Championship.
Challenge Cup. Kevin Blake (Captain 1989), Keith Bardon (Winner 1989) and Pat Smyth (Winner 1990 & 1991).
| Year | Winners | ||
| 2024 | Richard Hoey | ||
| 2023 | Richard Temperley | ||
| 2022 | Pat Walsh | ||
| 2021 | Mark O'Connell | ||
| 2020 | David Enraght-Moony | ||
| 2019 | Charlie Allen | ||
| 2018 | James Lawler | ||
| 2017 | Cian O'Sullivan | ||
| 2016 | Brian McCarthy | ||
| 2015 | Tom Wallace | ||
| 2014 | Finn Howley | ||
| 2013 | Gavin Homan | ||
| 2012 | James Mountjoy | ||
| 2011 | Morgan Duke | ||
| 2010 | Jim Byrne | ||
| 2009 | Paul Kirwan | ||
| 2008 | Robert Barrett | ||
| 2007 | Greg Leech | ||
| 2006 | John Barrett | ||
| 2005 | Denis Ryan | ||
| 2004 | M. Hoey | ||
| 2003 | G. Leech | ||
| 2002 | D. Devine | ||
| 2001 | F. Herriot | ||
| 2000 | D.McCarthy | ||
| 1999 | A.P. Byrne | ||
| 1998 | D.V. O'Meara | ||
| 1997 | Paul Smyth | ||
| 1996 | A.P. Byrne | ||
| 1995 | B.J. Molloy | ||
| 1994 | J. Keane | ||
| 1993 | L.G. Andrews | ||
| 1992 | D. MacManus | ||
| 1991 | Pat Smyth | ||
| 1990 | Pat Smyth | ||
| 1989 | K. Bardon | ||
| 1988 | P.A. O'Brien | ||
| 1987 | P.A. O'Brien | ||
| 1986 | D. O'Neill | ||
| 1985 | J. Bailie | ||
| 1984 | J. O'Doherty | ||
| 1983 | M. Glynn | ||
| 1982 | A.P. Byrne | ||
| 1981 | P.D. Bardon | ||
| 1980 | J. King | ||
| 1979 | D.J. O'Neill | ||
| 1978 | D.G. Carroll | ||
| 1977 | T.F. McCarron | ||
| 1976 | M.J. Cullen | ||
| 1975 | N. Duke | ||
| 1974 | C.J. Byrne | ||
| 1973 | T.J. Cox | ||
| 1972 | S.H. Pigot | ||
| 1971 | C.J. Carlos | ||
| 1970 | K.J. Blake | ||
| 1969 | J.P. Murray | ||
| 1968 | T.F. McCarron | ||
| 1967 | J.R. Anderson | ||
| 1966 | J. McCarron | ||
| 1965 | P. Farren | ||
| 1964 | G. Chadwick | ||
| 1963 | J.R. Hunter | ||
| 1962 | J.D. Buggle | ||
| 1961 | J.P. Murray | ||
| 1960 | G.H. Crawford | ||
| 1959 | T.F. Macken | ||
| 1958 | S.K. McComas | ||
| 1957 | P.M. Webb | ||
| 1956 | J.R. Hunter | ||
| 1955 | R. Redding | ||
| 1954 | A.C. Preston | ||
| 1953 | A.C. Preston | ||
| 1952 | S.K. McComas | ||
| 1951 | L.P. Bannon | ||
| 1950 | Col.J. McCaffrey | ||
| 1949 | G. Brownlee | ||
| 1948 | G. Brownlee | ||
| 1947 | C. White | ||
| 1946 | M.J. Cullen | ||
| 1945 | D.M. Saunders | ||
| 1944 | T.A. Mulcahy | ||
| 1943 | R.B. Wellwood | ||
| 1942 | F. O'Rourke | ||
| 1941 | T.D. Purcell | ||
| 1940 | P.F. Murray | ||
| 1939 | G.C. Higginbotham | ||
| 1938 | E.V. McCormick | ||
| 1937 | P.F. Murray | ||
| 1936 | P.B. Murray | ||
| 1935 | J.F. Carton | ||
| 1934 | H.G. Moore | ||
| 1933 | R.A. Ross Todd | ||
| 1932 | W. Thorpe | ||
| 1931 | G.N. Murphy | ||
| 1930 | A.E. Keatinge | ||
| 1929 | G. Walker | ||
