| Season | Club |
| 1998 | Seaton Carew |
| 1999 | Redcar |
| 2000 | Preston |
| 2001 | Blackhall |
| 2002 | Great Ayton |
| 2003 | Wolviston |
| 2004 | Middlesbrough |
| 2005 | Hartlepool |
| 2006 | Wolviston |
| 2007 | Middlesbrough |
| 2008 | Yarm |
| 2009 | Normanby Hall |
| 2010 | Normanby Hall |
| 2011 | Barnard Castle |
| 2012 | Middlesbrough |
| 2013 | Barnard Castle |
| 2014 | Darlington |
| 2015 | Stokesley |
| 2016 | Marton |
| 2017 | Normanby Hall |
| 2018 | Normanby Hall |
| 2019 | No competition |
| 2020 | No competition - CoronaVirus |
|
| Number of Wins | Club |
| 4 | Normanby Hall |
| 3 | Middlesbrough |
| 2 | Barnard Castle |
| 2 | Wolviston |
| 1 | Blackhall |
| 1 | Darlington |
| 1 | Great Ayton |
| 1 | Hartlepool |
| 1 | Marton |
| 1 | No competition |
| 1 | No competition - CoronaVirus |
| 1 | Preston |
| 1 | Redcar |
| 1 | Seaton Carew |
| 1 | Stokesley |
| 1 | Yarm |
|