Previous Junior A Cup Winners
Junior Challenge Cup presented by S.E.Saunders
January 1918
| 1918 | Cowes A |
| 1919 | Cowes A |
| 1920 | |
| 1921 | St Helens BS |
| 1922 | Rookwood |
| 1923 | Binstead |
| 1924 | |
| 1925 | Binstead |
| 1926 | |
| 1927 | |
| 1928 | |
| 1929 | Ryde Upper Old Boys |
| 1930 | W.C.United Methodists |
| 1931 | Ryde Rovers |
| 1932 | Ryde Rovers |
| 1933 | Swanmore |
| 1934 | West Wight Social |
| 1935 | Seaview |
| 1936 | Carisbrooke |
| 1937 | Carisbrooke |
| 1942 | East Cowes |
| 1946 | West Wight |
| 1947 | Yarmouth |
| 1948 | Haylands |
| 1949 | Haylands |
| 1950 | Barton Sports |
| 1951 | Barton Sports |
| 1952 | Wootton |
| 1953 | Saro Sports |
| 1954 | Parkhurst |
| 1955 | Water Transport R.A.S.C. |
| 1956 | Haylands |
| 1957 | Haylands |
| 1958 | Ventnor |
| 1959 | Barton Sports |
| 1960 | Oakfield |
| 1961 | Ryde United |
| 1962 | Haylands |
| 1963 | Wroxall |
| 1964 | Northwood S.J. |
| 1965 | Oakfield |
| 1966 | Wootton |
| 1967 | Whitecroft Hospital |
| 1968 | Whitecroft Hospital |
| 1969 | Bembridge |
| 1970 | Ryde County Old Boys |
| 1971 | Ventnor |
| 1972 | Wootton |
| 1973 | Northwood S.J. |
| 1974 | St Helens B.S. |
| 1975 | Bembridge |
| 1976 | Yarmouth Town |
| 1977 | Whites Sports |
| 1978 | Brading Youth |
| 1979 | Bembridge |
| 1980 | St Helens B.S. |
| 1981 | St Helens B.S. |
| 1982 | Ryde Sports |
| 1983 | Bembridge |
| 1984 | B.H.C.Sports |
| 1985 | Shanklin Reserves |
| 1986 | Plessey |
| 1987 | Seaview |
| 1988 | Sandown |
| 1989 | Seaview |
| 1990 | Brading Town A |
| 1991 | W & B Sports |
| 1992 | Carisbrooke United |
| 1993 | St Helens B.S. |
| 1994 | West Wight Reserves |
| 1995 | Westlands |
| 1996 | Osborne Coburg |
| 1997 | Seaview |
| 1998 | Shanklin Reserves |
| 1999 | Oakfield |
| 2000 | St Helens B.S. |
| 2001 | Niton |
| 2002 | Carisbrooke United |
| 2003 | Plessey |
| 2004 | Plessey |
| 2005 | Ventnor |
| 2006 | Brading Town Reserves |
| 2007 | Shanklin |
| 2008 | Vics Vets |
| 2009 | W & B Sports |
| 2010 | Ventnor |
| 2011 | Sandown |
| 2012 | Osborne Coburg |
| 2013 | W & B Sports |
| 2014 | W & B Sports |
| 2015 | Bembridge |
| 2016 | Brighstone |
| 2017 | ECS Reserves |
| 2018 | Pan Sports |
| 2019 | Ryde Saints |
| 2020 | Not played due to Covid19. |
| 2021 | Not played due to Covid 19. |
| 2022 | Pan Community |
| 2023 | Ventnor FC |
| 2024 | Osborne Coburg |