| Division 5 | |
| 1995 | Cropston Second XI |
| 1996 | Langtons |
| Division 4 | |
| 1997 | Leicester Banks Second XI |
| 1998 | Langtons Second XI |
| 1999 | Kibworth Second XI |
| 2000 | Leicester Ivanhoe Second XI |
| 2001 | Loughborough Town Second XI |
| 2002 | Loughborough Town Second XI |
| 2003 | Kibworth Second XI |
| 2004 | Gracedieu Park |
| 2005 | Market Bosworth |
| 2006 | Hinckley Amateur |
| 2007 | Barkby United |
| 2008 | Rothley Park |
| 2009 | Sileby Town Second XI |
| 2010 | Enderby |
| 2011 | Newtown Linford Second XI |
| 2012 | Mountsorrel Castle |
| 2013 | Uppingham Town |
Richard Holdridge
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