| 1927 | Dinnington P.M. |
| 1928 | Whitwell U.M.C. |
| 1929 | Whitwell U.M.C. |
| 1930 | Retford Second XI |
| 1931 | Rampton S.I.S.R.C. |
| 1932 | Bolsover Colliery Second XI |
| 1933 | Thurcroft Main Second XI |
| 1934 | Manton Colliery Second XI |
| 1935 | Worskop Co-operative Employees |
| 1936 | Wales Church Second XI |
| 1937 | Glapwell Colliery Second XI |
| 1938 | Waleswood Colliery |
| 1939 | Warsop Main Second XI |
| 1940-1948 | No competition |
| 1949 | Anston Second XI |
| Ordsall Wire Mills Second XI | |
| 1950 | Marshall’s Sports |
| 1951 | Marshall’s Sports |
| 1952 | Oates Sports |
| 1953 | Bothamsall |
| 1954 | Laxton Second XI |
| 1955 | Dinnington M.W. Second XI |
| 1956 | Anston Second XI |
| 1957 | Dinnington C.I. Second XI |
| 1958 | Milton |
| 1959 | Dinnington C.I. Second XI |
| 1960 | Weston |
| 1961 | Harthill Second XI |
| 1962 | Ollerton Colliery Second XI |
Thanks to Pete Grifiths