| 1955 | Rose Brothers Second XI |
| Laxton | |
| 1956 | Worksop Co-op Employees |
| 1957 | Clipstone Second XI |
| 1958 | Worksop Second XI |
| 1959 | Rufford |
| Whitwell Second XI | |
| 1960 | Worksop Co-op Employees |
| 1961 | Milton |
| 1962 | Gainsborough Britannia Second XI |
| 1963 | Clipstone Second XI |
| 1964 | Weston |
| 1965 | Killmarsh Second XI |
| 1966 | Mansfield Second XI |
| 1967 | Laxton |
| 1968 | Dinnington C I Second XI |
| Staveley Welfare Second XI | |
| 1969 | Ruston and Hornsby Second XI |
| 1970 | Waleswood |
| 1971 | Teversal and Silverhill Collieries Second XI |
| 1972 | Firbeck Main Colliery |
| 1973 | Creswell Colliery Second XI |
| 1974 | S and J Kitchen |
| 1975 | Sherwood Colliery Second XI |
| 1976 | Sheepbridge |
| 1977 | Welbeck Second XI |
| 1978 | Whitwell Second XI |
| 1979 | Clay Cross Second XI |
| 1980 | Bridon Second XI |
| 1981 | Rufford |
| 1982 | Grassmoor |
| 1983 | Glapwell Colliery Second XI |
| 1984 | Staveley Welfare |
| 1985 | Blidworth |
| 1986 | Milton |
| 1987 | Bolsover |
| 1988 | Alfreton |
| 1989 | ThoresbyPark |
| 1990 | Clipstone Welfare |
| 1991 | Kiveton Park |
| 1992 | Chesterfield |
| 1993 | Blyth |
| 1994 | Retford |
| 1995 | Worksop |
| 1996 | Kiveton Park |
| 1997 | Mansfield Hosiery Mills |
| 1998 | Bolsover |
| 1999 | Papplewick and Linby |
| 2000 | Ashover |
Thanks to Pete Griffiths