| Year | Winners |
| 2001 | Arnold Second XI |
| 2002 | Farnsfield Second XI |
| 2003 | Welbeck Colliery Second XI (Academy) |
| 2004 | Mansfield and Pleasley |
| 2005 | Caythorpe Second XI |
| 2006 | Retford Second XI |
| 2007 | Bridon Second XI |
| 2008 | Wiseton |
| 2009 | Clipstone Welfare |
| 2010 | Glapwell Colliery Second XI |
| 2011 | Milton |
| 2012 | Notts and Arnold Amateur Second XI |
| 2013 | Kiveton Park Colliery Second XI |
| 2014 | Roses |
| 2015 | Bawtry |
| 2016 | Waleswood Sports |
| 2017 | Retford |
| 2018 | Blyth |
| 2019 | Cuckney Third XI |
| 2020 |
| Division 3-A | Division 3-B |
| Worksop Second XI | Shirebrook |
|
| 2021 | Worksop Second XI |
