| 2001 | Bolsover Colliery Second XI | ||||
| 2002 | Sherwood Colliery | ||||
| 2003 | Welbeck Colliery Third XI | ||||
| 2004 | Clumber Park | ||||
| 2005 | Anston Second XI | ||||
| 2006 | Killamarsh Juniors Second XI | ||||
| 2007 | Nomads | ||||
| 2008 | Firbeck | ||||
| 2009 | Teversal Second XI | ||||
| 2010 | Rose Leisure | ||||
| 2011 | Clumber Park Second XI | ||||
| 2012 | Anston Third XI | ||||
| 2013 | Cuckney Third XI | ||||
| 2014 | South Normanton | ||||
| 2015 | Whitwell Second XI | ||||
| 2016 | Wiseton | ||||
| 2017 | Shirebrook | ||||
| 2018 | Papplewick and Linby Third XI | ||||
| 2019 | Bawtry Second XI | ||||
| 2020 |
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| 2021 | Grassmoor Worls Second XI |
Thanks to Pete Griffiths