| 1953 | Sun Engineers |
| 1954 | Scunthorpe Co-op |
| 1955 | Scunthorpe Nomads |
| 1956 | Sun Engineers |
| 1957 | Sun Engineers |
| 1958 | Sun Engineers |
| 1959 | Sun Engineers |
| 1960 | Sun Engineers |
| 1961 | Redbourn Second XI |
| 1962 | Sun Engineers |
| 1963 | Scunthorpe Co-op |
| 1964 | Firth Browns |
| 1965 | Crowle Sports |
| 1966 | Alkborough |
| 1967 | Alkborough |
| 1968 | Scunthorpe Co-op |
| 1969 | Nuform Sports |
| 1970 | Messingham |
| 1971 | Messingham |
| 1972 | Gunness |
| 1973 | Messingham |
| 1974 | Laughton |
| 1975 | Broughton |
| 1976 | Burton Stather |
| 1977 | Belton |
| 1978 | Messingham Second XI |
| 1979 | Hibaldstow |
| 1980 | Laughton |
| 1981 | West Butterwick |
| 1982 | Hibaldstow |
| 1983 | Kirton Lindsey |
| 1984 | Kirton Lindsey |
| 1985 | Belton Third XI |
| 1986 | Belton Third XI |
| 1987 | Gunness |
| 1988 | Belton Third XI |
| 1989 | Gunness |
| 1990 | Belton Third XI |
| 1991 | Nuform |
| 1992 | Burton Stather |
| 1993 | Normanby Park |
| 1994 | Gunness |
| 1995 | Normanby Park Works Third XI |
| 1996 | Laughton |
| 1997 | Nornamby Park Works Third XI |
| 1998 | Laughton |
| 1999 | Gunness |
| 2000 | Gunness |
| 2001 | Gunness |
| Outcasts | |
| 2002 | Outcasts Third XI |
| 2003 | Messingham Third XI |
| 2004 | Messingham Third XI |
| 2005 | Appleby Frodingham Third XI |
| 2006 | Caistor Cougars |
| 2007 | Caistor Cougars |
| 2008 | Cleethorpes Fifth XI |
| 2009 | Cleethorpes Fifth XI |
| 2010 | Cleethorpes Fifth XI |
| 2011 | Grimsby Town Third XI |
| 2012 | Scunthorpe Town Fourth XI |
| 2013 | Appleby Frodingham Third XI |
| 2014 | Appleby Frodingham Third XI |
| 2015 | Appleby Frodingham Third XI |
| 2016 | Appleby Frodingham Third XI |
| 2017 | Caistor Cougars |
| 2018 | Luddington Dons |
| 2019 | Morton |
| 2020 | no competition |
| 2021 | Scunthorpe Town Development XI |
| 2022 | Scunthorpe Town Development XI |
Brett Smith