| Year | Winners | Runners up |
| 2010/2011 | The Plough | The Wye Emms |
| 2009 - 2010 | Wye Emms | Cosmos |
| 2008 - 2009 | Bombers | Cosmos |
| 2007 - 2008 | Twyning C.C. | Cleeve Hillbillies |
| 2006 - 2007 | Swifts | Twyning C.C. |
| 2005 - 2006 | Wye Emms | Plough |
| 2004 - 2005 | Bombers | Throwouts |
| 2003 - 2004 | Cosmos | Rollers |
| 2002 - 2003 | Wye Emms | Throwouts |
| 2001 - 2002 | Wye Emms | Twyning C.C. |
| 2000 - 2001 | Ashton C.C. | Twyning C.C. |
| 1999 - 2000 | Wye Emms | Throwouts |
| 1998 - 1999 | Forthampton C.C. | Twyning C.C. |
| 1997 - 1998 | Cosmos | Crusaders |
| 1996 - 1997 | Wye Emms | Throwouts |
| 1995 - 1996 | Bishops | Rollers |
| 1994 - 1995 | Beechmen | Wye Emms |
| 1993 - 1994 | Swifts | Bishops |
| 1992 - 1993 | Swifts | Wye Emms |
| 1991 - 1992 | Wye Emms | Shunters |
| 1990 - 1991 | Gamecocks | Wye Emms |
| 1989 - 1990 | Gamecocks | Rebels |
| 1988 - 1989 | Cosmos | Rebels |
| 1987 - 1988 | Swifts | Plough C.L. |
| 1986 - 1987 | Swifts | Plough C.L. |
| 1985 - 1986 | Swifts | Twyning C.C. |
| 1984 - 1985 | Forthampton C.C. | Swifts |
| 1983 - 1984 | Gamecocks | Royal Oak |
| 1982 - 1983 | Plough C.L. | Electrolytes |
| 1981 - 1982 | Forthampton C.C. | Swifts |
| 1980 - 1981 | Cleeve AFC | Smurfs |
| 1979 - 1980 | Swifts | Gamescocks |
| 1978 - 1979 | Plough C.L. | Electrolytes |
| 1977 - 1978 | Cavalliers | |
| 1976 - 1977 | Rebels | |
| 1975 - 1976 | Cleeve AFC | |
| 1974 - 1975 | Village Inn | |
| 1973 - 1974 | Bishops | |
| 1972 - 1973 | Bishops | |
| 1971 - 1972 | Swifts | |
| 1970 - 1971 | Village Inn | |
| 1969 - 1970 | Wanderers | |
| 1968 - 1969 | Gamecocks | |
| 1967 - 1968 | Pendock Ramblers | |
| 1966 - 1967 | Swan Inn | |
| 1965 - 1966 | Gamecocks | |
| 1964 - 1965 | Cleeve AFC | |
| 1963 - 1964 | Forthampton C.C. | |
| 1962 - 1963 | Cleeve AFC | |
| 1961 - 1962 | Wytonians | |
| 1960 - 1961 | Shutter Inn |