| 1969 | Hykeham |
| 1970 | Cleethorpes |
| 1971 | Scunthorpe Town |
| 1972 | Saxilby |
| 1973 | Hykeham |
| 1974 | Grimsby Town |
| 1975 | Scunthorpe Town |
| 1976 | Messingham |
| 1977 | Holton Le Clay |
| 1978 | Cromweel Drewery |
| 1979 | Ruston Bucyrus |
| 1980 | Appleby Frodingham |
| 1981 | Alkborough |
| 1982 | Skegness |
| 1983 | Normanby Park |
| 1984 | Louth |
| 1985 | Market Rasen |
| 1986 | Skegness |
| 1987 | Broughton |
| 1988 | Hykeham |
| 1989 | Skegness |
| 1990 | Alford |
| 1991 | Alkborough |
| 1992 | South Kelsey |
| 1993 | Belton |
| 1994 | South Kelsey |
| 1995 | South Kelsey |
| 1996 | Market Rasen |
| 1997 | Owmby |
| 1998 | Skegness |
| 1999 | Nettleham |
| 2000 | Haxey |
| 2001 | Normanby Park Works |
| 2002 | South Kelsey |
| 2003 | Grimsby Town |
| 2004 | Cleethorpes Second XI |
| 2005 | Cherry Willingham |
| 2006 | Cherry Willingham |
| 2007 | Horncastle |
| 2008 | Cherry Willingham |
| 2009 | Cleethorpes Third XI |
| 2010 | Cherry Willingham |
| 2011 | Scothern |
| 2012 | Bracebridge Heath Second XI |
| 2013 | Broughton |
| 2014 | Scothern |
| 2015 | Outcasts |
| 2016 | Alkborough |
| 2017 | Outcasts |
| 2018 | Hartsholme |
| 2019 | Holton Le Clay |
| 2020 | No competition |
| 2021 | Outcasts |
| 2022 | Barton Town |
| 2023 | |
| 2024 | Messingham |
Brett Smith