| Season | Club |
| 1988 | Middlesbrough |
| 1989 | Hartlepool |
| 1990 | Hartlepool |
| 1991 | Middlesbrough |
| 1992 | Redcar |
| 1993 | Thornaby |
| 1994 | Guisborough |
| 1995 | Thornaby |
| 1996 | Norton |
| 1997 | Hartlepool |
| 1998 | Guisborough |
| 1999 | Richmondshire |
| 2000 | Saltburn |
| 2001 | Redcar |
| 2002 | Middlesbrough |
| 2003 | Middlesbrough |
| 2004 | Saltburn |
| 2005 | Normanby Hall |
| 2006 | Guisborough |
| 2007 | Marton |
| 2008 | Great Ayton |
| 2009 | Marton |
| 2010 | Richmondshire |
| 2011 | Guisborough |
| 2012 | Great Ayton |
| 2013 | Great Ayton |
| 2014 | Great Ayton |
| 2015 | Seaton Carew |
| 2016 | Richmondshire |
| 2017 | Barnard Castle |
| 2018 | Barnard Castle |
| 2019 | Durham Academy |
| 2020 | Hartlepool |
| 2021 | Barnard Castle |
| 2022 | Richmondshire |
| 2023 | Richmondshire |
| 2024 | Middlesbrough |
| 2025 | Barnard Castle |
|
| Number of Wins | Club |
| 5 | Middlesbrough |
| 5 | Richmondshire |
| 4 | Barnard Castle |
| 4 | Great Ayton |
| 4 | Guisborough |
| 4 | Hartlepool |
| 2 | Marton |
| 2 | Redcar |
| 2 | Saltburn |
| 2 | Thornaby |
| 1 | Durham Academy |
| 1 | Normanby Hall |
| 1 | Norton |
| 1 | Seaton Carew |
|