| 1937 | Appleby Frodingham |
| 1938 | Messingham |
| 1939 | Appleby Frodingham |
| 1940 | West Butterwick |
| 1941 | Messingham |
| 1942 | Messingham |
| 1943 | Scunthorpe Nomads |
| 1944 | Scunthorpe Nomads |
| 1945 | Scawby |
| 1946 | West Butterwick |
| 1947 | Scunthorpe Co-Op |
| 1948 | Winteringham |
| 1949 | West Butterwick |
| 1950 | Sun Engineers |
| 1951 | Sun Engineers |
| 1952 | West Butterwick |
| 1953 | Broughton |
| 1954 | Lysaghts |
| 1955 | Firth Browns |
| 1956 | West Butterwick |
| 1957 | West Butterwick |
| 1958 | Gunness |
| 1959 | Alkborough |
| 1960 | Gunness |
| 1961 | Gunness |
| 1962 | Belton |
| 1963 | Firth Browns |
| 1964 | Alkborough |
| 1965 | Scotter |
| 1966 | Scotter |
| 1967 | Alkborough |
| 1968 | Ore Mining Branch |
| 1969 | Normanby Park |
| 1970 | Nuform Sports |
| 1971 | Messingham |
| 1972 | Keadby Power Station |
| 1973 | Messingham |
| 1974 | Appleby Frodingham |
| 1975 | Appleby Frodingham |
| 1976 | Nuform Sports |
| 1977 | Broughton |
| 1978 | Appleby Frodingham |
| 1979 | Laughton |
| 1980 | Scunthorpe Town |
| 1981 | Normanby Park Works |
| 1982 | Normanby Park Works |
| 1983 | Laughton |
| 1984 | Laughton |
| 1985 | Belton |
| 1986 | Broughton |
| 1987 | Normanby Park |
| 1988 | Messingham |
| 1989 | Alkborough |
| 1990 | Alkborough |
| 1991 | Laughton |
| 1992 | Appleby Frodingham |
| 1993 | Bottesford Town |
| 1994 | Laughton |
| 1995 | Appleby Frodingham |
| 1996 | unknown |
| 1997-2003 | no competition |
| 2024 | Alkborough Midweek XI |
Brett Smith, Neil Simpson