| Vice President's Challenge Bowl | |||
| Year | Winner(s) | ||
| 2021 | A Towle | ||
| 2019 | M Spiller | ||
| 2018 | G Stewart | ||
| 2017 | B Bennett | ||
| 2016 | M Easton | ||
| 2015 | M Engles | ||
| 2014 | D Snell | ||
| 2013 | S Ridal | ||
| 2012 | MJG Penney | ||
| 2011 | R Plumb | ||
| 2010 | J Allen | ||
| 2009 | D Crawshaw | ||
| 2008 | M Simpkins | ||
| 2007 | A Slater | ||
| 2006 | T Daniels | ||
| 2005 | A Cummings | ||
| 2004 | J Cichocki | ||
| 2003 | N Pugh | ||
| 2002 | PR Wright | ||
| 2001 | PR Wright | ||
| 2000 | CR Jones | ||
| 1999 | A Osborne | ||
| 1998 | PA Kubiak | ||
| 1997 | IA Booth | ||
| 1996 | AS Beale | ||
| 1995 | J Bruce | ||
| 1994 | P Moore | ||
| 1993 | AC Brown | ||
| 1992 | B Raggett | ||
| 1991 | BR Boughey | ||
| 1990 | P Kubiak | ||
| 1989 | DG Moore | ||
| 1988 | A Conduit | ||
| 1987 | GJD Johnstone | ||
| 1986 | RJ Callaghan | ||
| 1985 | K Doyle | ||
| 1984 | PB Willis | ||
| 1983 | RD Waigh | ||
| 1982 | J Yarwood | ||
| 1981 | DI Black | ||
| 1980 | J Dixon | ||
| 1979 | DS Wightman | ||
| 1978 | FA Hardy | ||
| 1977 | PB Willis | ||
| 1976 | N Coates | ||
| 1975 | RM Alsop | ||
| 1974 | EI Bell | ||
| 1973 | RGC Davies | ||
| 1972 | ST Gibbon | ||
| 1971 | AB Wright | ||
| 1970 | NA Williamson | ||
| 1969 | D Walker | ||
| 1968 | BW Mayers | ||
| 1967 | W Brown | ||
| 1966 | AD Pook | ||
| 1965 | NA Williamson | ||
| 1964 | FA Hardy | ||
| 1963 | W Brown | ||
| 1962 | AD Spalding | ||
| 1961 | A Atkins | ||
| 1960 | W Brown | ||
| 1959 | H Wright | ||
| 1958 | FA Simpson | ||
| 1957 | F Dennett | ||
| 1956 | SG Smith | ||
| 1955 | WH Jones | ||
| 1954 | T Henderson | ||
| 1953 | GA Simister | ||
| 1952 | FA Simpson | ||
| 1951 | WH Jones | ||
| 1950 | JJS Kennaugh | ||
| 1949 | N Percival | ||
| 1948 | N Haslam | ||
| 1947 | H Nuttall | ||
| 1946 | JY Dearden | ||
| 1945 | AD Gough | ||
| 1944 | A Noel-Streat | ||
| 1943 | FD Hill | ||
| 1942 | George Clarke | ||
| 1941 | CE Holt | ||
| 1940 | H Boak | ||
| 1939 | JS Holmes | ||
| 1938 | FW Spencer | ||
| 1937 | GH Taylor | ||
| 1936 | L Wharton | ||
| 1935 | F Wroe | ||
| 1934 | R Nish | ||
| 1933 | Oliver Mee | ||
| 1932 | AG Griffiths | ||
| 1931 | CE Holt | ||
| 1930 | AG Griffiths | ||
| 1929 | CW Franks | ||
| 1928 | JM Worthington | ||
| 1927 | HG Barrow | ||
| 1926 | EH Mee | ||
| 1925 | NM Birtles | ||
| 1924 | JA Dewar | ||
| 1923 | N Edmondson | ||
| 1922 | NG Myers | ||
| 1921 | D Jessop | ||
| 1920 | JA Kellett | ||
| 1919 | W Hayliss | ||
| 1918 | The Great War | ||
| 1917 | The Great War | ||
| 1916 | The Great War | ||
| 1915 | The Great War | ||
| 1914 | RF Cunningham | ||
Alderley Edge Golf Club