| 1963 | Ross Group |
| 1964 | Lysaughts |
| 1965 | Grimsby Town |
| 1966 | Grimsby Town |
| 1967 | Cleethorpes |
| 1968 | Cleethorpes |
| 1969 | Cleethorpes |
| 1970 | Ross Group |
| 1971 | Cleethorpes |
| 1972 | Appleby Frodiungham |
| 1973 | Cleethorpes |
| 1974 | Grimsby Town |
| 1975 | Cleethorpes |
| 1976 | Cleethorpes |
| 1977 | Normany Park Works |
| 1978 | Cleethorpes |
| 1979 | Hartsholme |
| 1980 | Cleethorpes |
| 1981 | Cleethorpes |
| 1982 | Grimsby Town |
| 1983 | Cleethorpes |
| 1984 | Grimsby Town |
| 1985 | Grimsby Town |
| 1986 | Hartsholme |
| 1987 | Hartsholme |
| 1988 | Grimsby Town |
| 1989 | Nomanby Park |
| 1990 | Lincoln Claytons |
| 1991 | Lincoln Claytons |
| 1992 | Market Rasen |
| 1993 | Lincoln Claytons |
| 1994 | Alkborough |
| 1995 | Messingham |
| 1996 | Belton |
| 1997 | Caistor Town |
| 1998 | Alkborough |
| 1999 | Grimsby Town |
| 2000 | Alkborough |
| 2001 | Owmby |
| 2002 | Owmby |
| 2003 | Cleethorpes Second XI |
| 2004 | Caistor Town |
| 2005 | Nettleham |
| 2006 | Alkborough |
| 2007 | Haxey |
| 2008 | Bracebridge Heath Second XI |
| 2009 | Hartsholme |
| 2010 | Messingham |
| 2011 | Haxey |
| 2012 | Scunthorpe Town |
| 2013 | Market Rasen |
| 2014 | Messingham |
| 2015 | Nettleham |
| 2016 | Cherry Willingham |
| 2017 | Scunthorpe Town |
| 2018 | Caistor Town |
| 2019 | Scothern |
| 2020 | No competition |
| 2021 | Nettleham |
| 2022 | Grimsby Town |
Brett Smith