| Season | Club |
| 1998 | Great Ayton |
| 1999 | Hartlepool |
| 2000 | Bedale |
| 2001 | Nunthorpe |
| 2002 | Darlington RA |
| 2003 | Blackhall |
| 2004 | Middlesbrough |
| 2005 | Marske |
| 2006 | Marske |
| 2007 | Northallerton |
| 2008 | Marske |
| 2009 | Northallerton |
| 2010 | Northallerton |
| 2011 | Darlington RA |
| 2012 | Great Ayton |
| 2013 | Hartlepool |
| 2014 | Stokesley |
| 2015 | Stokesley |
| 2016 | Barnard Castle |
| 2017 | Wolviston |
| 2018 | Rockliffe Park |
| 2019 | Guisborough |
| 2020 | Barnard Castle |
| 2021 | Saltburn |
| 2022 | Northallerton |
| 2023 | Hartlepool |
| 2024 | Barnard Castle |
| 2025 | Norton |
|
| Number of Wins | Club |
| 4 | Northallerton |
| 3 | Barnard Castle |
| 3 | Hartlepool |
| 3 | Marske |
| 2 | Darlington RA |
| 2 | Great Ayton |
| 2 | Stokesley |
| 1 | Bedale |
| 1 | Blackhall |
| 1 | Guisborough |
| 1 | Middlesbrough |
| 1 | Norton |
| 1 | Nunthorpe |
| 1 | Rockliffe Park |
| 1 | Saltburn |
| 1 | Wolviston |
|