| | Winners | Runners Up (First Cup Awards) |
| 1948 | Ex Servicmens | |
| 1949 | Hailsham | |
| 1950 | Ex Servicmens | |
| 1951 | Fishermens | |
| 1952 | Fishermens | |
| 1953 | Fishermens | |
| 1954 | Ex Servicmens | |
| 1955 | Police Athletic | |
| 1956 | Eastbourne Constitutional | |
| 1957 | Eastbourne Constitutional | |
| 1958 | Ex Servicmens | |
| 1959 | Eastbourne Constitutional | |
| 1960 | Eastbourne Constitutional | |
| 1961 | Ex Servicmens | |
| 1962 | Southdown | |
| 1963 | Ex Servicmens | |
| 1964 | Hailsham | |
| 1965 | Ex Servicmens | |
| 1966 | E.W.M.C. | |
| 1967 | Roselands | |
| 1968 | Roselands | |
| 1969 | Eastbourne RB Legion | |
| 1970 | Eastbourne Constitutional | |
| 1971 | Eastbourne Constitutional | |
| 1972 | Eastbourne Constitutional | |
| 1973 | Eastbourne Constitutional | |
| 1974 | E.W.M.C. | |
| 1975 | Meads | |
| 1976 | E.W.M.C. | |
| 1977 | Hailsham MI | |
| 1978 | E.W.M.C. | |
| 1979 | Eastbourne Constitutional | |
| 1980 | Eastbourne Constitutional | D.E.B. A |
| 1981 | Fishermens | Hellingly B |
| 1982 | Con | Meads A |
| 1983 | E.W.M.C. | Hailsham MI A |
| 1984 | E.W.M.C. | Con B |
| 1985 | Hailsham Club | R.N.O.C. A |
| 1986 | Hailsham MI | Polegate RBL A |
| 1987 | E.W.M.C. | Police A |
| 1988 | Hailsham MI | Q Ball A |
| 1989 | Malthouse | E/B Con A |
| 1990 | Q Ball | Hailsham MI A |
| 1991 | Hailsham MI | Malthouse |
| 1992 | Hailsham MI | Malthouse |
| 1993 | Malthouse E | Malthouse |
| 1994 | Q Ball | E.W.M.C. |
| 1995 | E.W.M.C. | Polegate RBL A |
| 1996 | Q Ball | E.W.M.C. |
| 1997 | Dolphin | Q Ball B |
| 1998 | Dolphin | Dolphin A |
| 1999 | Fishermens D | Q Ball A |
| 2000 | E.W.M.C. | Polegate RBL A |
| 2001 | Dolphin | Q Ball F |
| 2002 | Dolphin A | Q Ball A |
| 2003 | Q Ball A | Hailsham MI C |
| 2004 | Q Ball A | Langney |
| 2005 | Dolphin A | Polegate A |
| 2006 | Q Ball A | Dolphin A |
| 2007 | Dolphin A | Q Ball A |
| 2008 | Dolphin A | Meads A |
| 2009 | Polegate RBL A | Dolphin A |
| 2010 | Meads A | Polegate RBL A |