| Season | Club |
| 2002 | Saltburn |
| 2003 | Thornaby |
| 2004 | Wolviston |
| 2005 | Maltby |
| 2006 | Stockton |
| 2007 | Barnard Castle |
| 2008 | Barnard Castle |
| 2009 | Norton |
| 2010 | Marton |
| 2011 | Marton |
| 2012 | Barnard Castle |
| 2013 | Stokesley |
| 2014 | Saltburn |
| 2015 | Richmondshire |
| 2016 | Richmondshire |
| 2017 | Guisborough |
| 2018 | Stokesley |
| 2019 | Hartlepool |
| 2020 | No competition - CoronaVirus |
| 2021 | Hartlepool |
| 2022 | Great Ayton |
| 2023 | Sedgefield |
|
| Number of Wins | Club |
| 3 | Barnard Castle |
| 2 | Hartlepool |
| 2 | Marton |
| 2 | Richmondshire |
| 2 | Saltburn |
| 2 | Stokesley |
| 1 | Great Ayton |
| 1 | Guisborough |
| 1 | Maltby |
| 1 | No competition - CoronaVirus |
| 1 | Norton |
| 1 | Sedgefield |
| 1 | Stockton |
| 1 | Thornaby |
| 1 | Wolviston |
|