| 1955 | Langwith Second XI |
| 1956 | Rose Brothers Second XI |
| 1957 | Rose Brothers Second XI |
| 1958 | Worksop Co-op Employees |
| 1959 | Steetley Second XI |
| 1960 | Worksop Second XI |
| 1961 | Dinnington Miners’ Welfare |
| 1962 | Steetley Second XI |
| 1963 | Steetley Second XI |
| 1964 | Steetley Second XI |
| 1965 | Steetley Second XI |
| 1966 | Worksop Second XI |
| 1967 | Steetley Second XI |
| 1968 | Chesterfield Second XI |
| 1969 | Cuckney |
| 1970 | Worksop Second XI |
| 1971 | Steetley Second XI |
| 1972 | Steetley Second XI |
| 1973 | Worksop Second XI |
| 1974 | Teversal and Silverhill Collieries Second XI |
| 1975 | Firbeck |
| 1976 | Retford Second XI |
| 1977 | Retford Second XI |
| 1978 | Worksop Second XI |
| 1979 | Steetley Second XI |
| 1980 | Kiveton Park Second XI |
| 1981 | Waleswood |
| 1982 | Firbeck |
| 1983 | Bridon Second XI |
| 1984 | Bridon |
| 1985 | Worksop |
| 1986 | Welbeck Colliery |
| 1987 | Welbeck Colliery |
| 1988 | Welbeck Colliery |
| 1989 | Farnsfield |
| 1990 | Farnsfield |
| 1991 | Farnsfield |
| 1992 | Farnsfield |
| 1993 | Welbeck Colliery |
| 1994 | Caythorpe |
| 1995 | Welbeck Colliery |
| 1996 | Rerford |
| 1997 | Welbeck Colliery |
| 1998 | Farnsfield |
| 1999 | Bridon |
| 2000 | Bridon |
With thanks to Pete Griffiths