| Season | Club |
| 2006 | Guisborough |
| 2007 | Guisborough |
| 2008 | Great Ayton |
| 2009 | Richmondshire |
| 2010 | Great Ayton |
| 2011 | Bishop Auckland |
| 2012 | Stokesley |
| 2013 | Great Ayton |
| 2014 | Barnard Castle |
| 2015 | Hartlepool |
| 2016 | Great Ayton |
| 2017 | Stokesley |
| 2018 | Richmondshire |
| 2019 | Billingham Synthonia |
| 2020 | No competition - CoronaVirus |
| 2021 | Barnard Castle |
| 2022 | Thornaby |
| 2023 | Richmondshire |
|
| Number of Wins | Club |
| 4 | Great Ayton |
| 3 | Richmondshire |
| 2 | Barnard Castle |
| 2 | Guisborough |
| 2 | Stokesley |
| 1 | Billingham Synthonia |
| 1 | Bishop Auckland |
| 1 | Hartlepool |
| 1 | No competition - CoronaVirus |
| 1 | Thornaby |
|