| Season | Club |
| 2006 | Redcar |
| 2007 | Hartlepool |
| 2008 | Marton |
| 2009 | Marske |
| 2010 | Great Ayton |
| 2011 | Maltby |
| 2012 | Wolviston |
| 2013 | Middlesbrough |
| 2014 | Wolviston |
| 2015 | Barnard Castle |
| 2016 | Wolviston |
| 2017 | Wolviston |
| 2018 | Northallerton |
| 2019 | Marton |
| 2020 | No competition - CoronaVirus |
| 2021 | Barnard Castle |
| 2022 | Barnard Castle |
| 2023 | Barnard Castle |
|
| Number of Wins | Club |
| 4 | Barnard Castle |
| 4 | Wolviston |
| 2 | Marton |
| 1 | Great Ayton |
| 1 | Hartlepool |
| 1 | Maltby |
| 1 | Marske |
| 1 | Middlesbrough |
| 1 | No competition - CoronaVirus |
| 1 | Northallerton |
| 1 | Redcar |
|