Over 60’s League Division Two
| 1991 / 92 | LOUTH |
| 1992 / 93 | SPALDING |
| 1993 / 94 | HORNCASTLE |
| 1994 / 95 | GRANTHAM |
| 1995 / 96 | HORNCASTLE |
| 1996 / 97 | LOUTH |
| 1997 / 98 | SLEAFORD |
| 1998 / 99 | DUNHOLME |
| 1999 / 00 | SKEGNESS |
| 2000 / 01 | HORNCASTLE |
| 2001 / 02 | LOUTH |
| 2002 / 03 | LINCOLN "B" |
| 2003 / 04 | HORNCASTLE |
| 2004 / 05 | LONG SUTTON |
| 2005 / 06 | LOUTH |
| 2006 / 07 | LINCOLN "B" |
| 2007 / 08 | LONG SUTTON |
| 2008 / 09 | DUNHOLME |
| 2009 / 10 | LINCOLN "B" |
| 2010 / 11 | LOUTH |
| 2011 / 12 | SPALDING |
| 2012 / 13 | LOUTH |
| 2013 / 14 | SPALDING |
| 2014 / 15 | SKEGNESS "A" |
| 2015 / 16 | LOUTH |
| 2016 / 17 | BOSTON |
| 2017 / 18 | HORNCASTLE |
| 2018 / 19 | STAMFORD |