| YEAR | WINNERS | FINALISTS |
| 1946-1947 | St Athan East | St Athan West |
| 1947-1948 | Hirwaun Welfare | G.K.B. & Nettlefold |
| 1948-1949 | Pentre Athletic | Tonyrefail |
| 1949-1950 | Tonyrefail Welfare | Dinas Corries |
| 1950-1951 | Newport Count "A" | Taffs Well FC |
| 1951-1952 | Tonyrefail Welfare | Dinas Corries |
| 1952-1953 | Ynysybwl | Taffs Well FC |
| 1953-1954 | Taffs Well | Fleur-de-Lys |
| 1954-1955 | Penarth Town | Cardiff City "A" |
| 1955-1956 | Gilfach Welfare | RAF St Athan West |
| 1956-1957 | Guest Keen | Fleur-de-Lys |
| 1957-1958 | Cwmbach Sports | Guest Keen |
| 1958-1959 | Ystrad Athletic | Hirwaun Welfare |
| 1959-1960 | Cardiff City | Hirwaun Welfare |
| 1960-1961 | Guest Keen | Cwmbach Sports |
| 1961-1962 | Penrhiwceiber | Guest Keen |
| 1962-1963 | Caerau Rangers | Llanharan |
| 1963-1964 | Pyrene | Tredomen Works |
| 1964-1965 | Fleur-de-Lys | Hoover Sports |
| 1965-1966 | Bridgend Town | Pontllanfraith |
| 1966-1967 | Guest Keen | Beatus United |
| 1967-1968 | Ynyshir United | Dare Inglis |
| 1968-1969 | Sully | Bargoed Y.M.C.A. |
| 1969-1970 | Bridgend Town | Cilfynydd |
| 1970-1971 | Pontllanfraith | Penywaun Welfare |
| 1971-1972 | Penarth Town | Hoover Sports |
| 1972-1973 | Cardiff Corinthians | Taffs Well FC |
| 1973-1974 | Cambrian United | Cardiff Corinthians |
| 1974-1975 | Barry Plastics | Aber Valley |
| 1975-1976 | Cardiff Cosmos | Barry Plastics |
| 1976-1977 | Lake United | Hirwaun Welfare |
| 1977-1978 | Llantwit Fardre | Llantwit Major |
| 1978-1979 | Sully | Caerau Rangers |
| 1979-1980 | Cardiff Cosmos | Cilfynydd |
| 1980-1981 | Llantwit Major | Lake United |
| 1981-1982 | Bargoed United | Llwydcoed Welfare |
| 1982-1983 | Llantwit Fardre | Cardiff Cosmos |
| 1983-1984 | Llantwit Major | Cardiff Corinthians |
| 1984-1985 | AFC Cardiff | Ton Pentre & Gelli BC |
| 1985-1986 | Ely Rangers | Cardiff Corinthians |
| 1986-1987 | Llantwit Major | Bryntirion Athletic |
| 1987-1988 | A.F.C. Cardiff | Hoover Sports |
| 1988-1989 | British Steel | A.F.C. Cardiff |
| 1989-1990 | British Steel | Cardiff Civil Service |
| 1990-1991 | AFC Porth | Porthcawl Town |
| 1991-1992 | Penrhiwceiber Rangers | British Steel |
| 1992-1993 | Hoover Sports | British Steel |
| 1993-1994 | Hoover Sports | British Steel |
| 1994-1995 | Taffs Well FC | Barry Athletic |
| 1995-1996 | Cambrian United | Bryntirion Athletic |
| 1996-1997 | Cambrian United Sky Blues | Cardiff Civil Service |
| 1997-1998 | Bryntirion Athletic | British Steel |
| 1998-1999 | Dinas Powys | Bryntirion Athletic |
| 1999-2000 | British Steel | Barry Athletic |
| 2000-2001 | Llanbradach FC | Barry Athletic |
| 2001-2002 | British Steel | Llantwit Major |
| 2002-2003 | Cambrian & Clydach Vale BC | Llantwit Fardre AFC |
| 2003-2004 | Cardiff Draconians FC | Ynysddu Welfare |
| 2004-2005 | Kenfig Hill AFC | Cardiff Cosmos Portos |
| 2005-2006 | Cwmaman Institute | Aber Valley YMCA |
| W.JOHN OWEN CUP | ||
| 2006-2007 | Aber Valley YMCA | Abercynon Athletic |
| 2007-2008 | Aber Valley YMCA | Ynysddu Welfare Crusaders |
| 2008-2009 | Rhoose FC | Ynysddu Crusaders |