Previous Memorial Cup Winners
| The Royal Irish Rifles War Memorial Cup |
| Presented by the W.O’s, N.C.O’s
& Riflemen of the 1st Batallion The Royal Irish Rifles to the IWFA May 1920. |
| 1920 | East Cowes Vics FC |
| 1921 | |
| 1922 | The Irish Rifles FC. |
| 1923 | Cowes FC |
| 1924 | Bembridge FC |
| 1925 | Sandown & Lake United FC |
| 1926 | Newport FC |
| 1927 | Sandown FC |
| 1928 | Bembridge FC |
| 1929 | Sandown FC |
| 1930 | Sandown FC |
| 1931 | Cowes FC |
| 1932 | Bembridge FC |
| 1933 | East Cowes Vics FC |
| 1934 | Brading FC |
| 1935 | Sndown FC |
| 1936 | St Helens Sports FC |
| 1937 | Sandown FC |
| 1938 | Sandown |
| 1939 | Sandown FC |
| 1946 | Sandown FC |
| 1947 | Sandown FC |
| 1948 | West Wight FC |
| 1949 | West Wight FC |
| 1950 | West Wight FC |
| 1951 | Brading Town FC |
| 1952 | Brading Town FC |
| 1953 | West Wight FC |
| 1954 | West Wight FC |
| 1955 | Saro Sports FC |
| 1956 | Brading Town FC |
| 1957 | Sandown FC |
| 1958 | Parkhurst FC |
| 1959 | Parkhurst FC |
| 1960 | Brading Town FC |
| 1961 | West Wight FC |
| 1962 | St Helens B.S.FC |
| 1963 | Parkhurst FC |
| 1964 | Seaview FC |
| 1965 | Seaview FC |
| 1966 | Brading Town FC |
| 1967 | Seaview FC |
| 1968 | Brading Town FC |
| 1969 | Seaview FC |
| 1970 | B.H.C. Sports |
| 1971 | Shanklin FC |
| 1972 | Brading Town FC |
| 1973 | Barton Sports FC |
| 1974 | Barton Sports FC |
| 1975 | Shanklin FC |
| 1976 | B.H.C.Sports FC |
| 1977 | Newport FC |
| 1978 | Shanklin FC |
| 1979 | Shanklin FC |
| 1980 | Bembridge FC |
| 1981 | Newport FC |
| 1982 | Newport FC |
| 1983 | East Cowes Vics FC |
| 1984 | B.H.C.Sports FC |
| 1985 | W & B Sports FC |
| 1986 | W & B Sports FC |
| 1987 | Brading Town FC |
| 1988 | East Cowes Vics FC |
| 1989 | Shanklin FC |
| 1990 | Oakfield FC |
| 1991 | East Cowes Vics FC |
| 1992 | Binstead & COB FC |
| 1993 | W & B Sports FC |
| 1994 | Oakfield FC |
| 1995 | Binstead & COB FC |
| 1996 | Ryde Sports FC |
| 1997 | West Wight FC |
| 1998 | Shanklin FC |
| 1999 | Oakfield/Binstead & COB trophy shared |
| 2000 | Oakfield FC |
| 2001 | No competition because of weather. |
| 2002 | Oakfield FC |
| 2003 | Oakfield FC |
| 2004 | West Wight FC |
| 2005 | Binstead & COB FC |
| 2006 | Shanklin FC |
| 2007 | Shanklin FC |
| 2008 | Cowes Sports FC |
| 2009 | West Wight FC |
| 2010 | East Cowes Vics |
| 2011 | Oakfield |
| 2012 | Oakfield |
| 2013 | West Wight |
| 2014 | W & B Sports |
| 2015 | Northwood SJ |
| 2016 | W & B Sports |
| 2017 | Ventnor |
| 2018 | W & B Sports |
| 2019 | W & B Sports |
| 2020 | No competition due to Covid19. |
| 2021 | No competition due to Covid 19. |
| 2022 | Brading Town FC |
| 2023 | Shanklin FC |
| 2024 | Ventnor FC |