Previous Challenge Winners
The Isle of Wight Challenge Cup-presented by A.W.Lallow
| 1947 | Sandown FC |
| 1948 | East Cowes Vics FC |
| 1949 | Brading Town FC |
| 1950 | Sandown FC |
| 1951 | East Cowes Vics FC |
| 1952 | East Cowes Vics FC |
| 1953 | East Cowes Vics FC |
| 1954 | Newport FC |
| 1955 | Brading Town FC |
| 1956 | No competition |
| 1957 | No competition |
| 1958 | Newport FC |
| 1959 | Parkhurst FC |
| 1960 | West Wight FC |
| 1961 | Parkhurst FC |
| 1962 | Barton Sports FC |
| 1963 | Ryde Sports FC |
| 1964 | Ryde Sports FC |
| 1965 | Cowes Sports FC |
| 1966 | Parkhurst FC |
| 1967 | Parkhurst FC |
| 1968 | Seaview FC |
| 1969 | Brading Town FC |
| 1970 | Brading Town FC |
| 1971 | Barton Sports FC |
| 1972 | Brading Town FC |
| 1973 | Barton Sports FC |
| 1974 | Ryde County Old Boys |
| 1975 | Ventnor FC |
| 1976 | Barton Sports FC |
| 1977 | Barton Sports FC |
| 1978 | Shanklin FC |
| 1979 | Shanklin FC |
| 1980 | Shanklin FC |
| 1981 | East Cowes Vics FC |
| 1982 | West Wight FC |
| 1983 | Ryde Sports FC |
| 1984 | Shanklin FC |
| 1985 | East Cowes Vics FC |
| 1986 | Newport FC |
| 1987 | Newport FC |
| 1988 | East Cowes Vics FC |
| 1989 | Shanklin FC |
| 1990 | Shanklin FC |
| 1991 | East Cowes Vics FC |
| 1992 | East Cowes Vics FC |
| 1993 | Ryde Sports FC |
| 1994 | Ryde Sports FC |
| 1995 | Newport FC |
| 1996 | Shanklin FC |
| 1997 | Oakfield FC |
| 1998 | Oakfield FC |
| 1999 | Oakfield FC |
| 2000 | Binstead & COB FC |
| 2001 | Newport FC |
| 2002 | Shanklin FC |
| 2003 | West Wight FC |
| 2004 | West Wight FC |
| 2005 | West Wight FC |
| 2006 | Shanklin FC |
| 2007 | Cowes Sports FC |
| 2008 | West Wight FC |
| 2009 | West Wight FC |
| 2010 | West Wight FC |
| 2011 | West Wight FC |
| 2012 | East Cowes Vics FC |
| 2013 | Northwood SJ FC |
| 2014 | Niton FC |
| 2015 | Oakfield |
| 2016 | Shanklin |
| 2017 | W & B Sports |
| 2018 | W & B Sports |
| 2019 | W & B Sports |
| 2020 | Not played due to Covid19. |
| 2021 | Not played due to Covid19. |
| 2022 | Shanklin FC |
| 2023 | W & B Sports |