| Winner | |||
| Division 5 | |||
| 1998 | Bedale Second XI | ||
| 1999 | Carlton Towers Second XI | ||
| 2000 | Dringhouses Second XI | ||
| 2001 | Pickering Second XI | ||
| 2002 | Malton and Old Malton Second XI | ||
| 2003 | Pocklington Second XI | ||
| 2004 | Tadcaster Magnet Second XI | ||
| 2005 | Dunnington Second XI | ||
| 2006 | Sheriff Hutton Bridge Second XI | ||
| 2007 | Cawood | ||
| Division 5A | Division 5B | ||
| 2008 | Driffield Third XI | 2008 | Thorp Arch and Boston Spa Second XI |
| 2009 | Yapham | 2009 | Thirsk Second XI |
| 2010 | Huntington | 2010 | York IV |
| Division 5 | |||
| 2011 | Castleford Second XI | ||
| 2012 | Patrington | ||
| 2013 | Heworth Second XI | ||
Ian Sumner
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