| Season | Club |
| 1985 | Norton |
| 1986 | Hartlepool |
| 1987 | Thornaby |
| 1988 | Thornaby |
| 1989 | Middlesbrough |
| 1990 | Hartlepool |
| 1991 | Marske |
| 1992 | Stockton |
| 1993 | Marske |
| 1994 | Hartlepool |
| 1995 | Stockton |
| 1996 | Middlesbrough |
| 1997 | Middlesbrough |
| 1998 | Middlesbrough |
| 1999 | Redcar |
| 2000 | Middlesbrough |
| 2001 | Middlesbrough |
| 2002 | Hartlepool |
| 2003 | Hartlepool |
| 2004 | Redcar |
| 2005 | Marske |
| 2006 | Redcar |
| 2007 | Middlesbrough |
| 2008 | Normanby Hall |
| 2009 | Normanby Hall |
| 2010 | Normanby Hall |
| 2011 | Darlington RA |
| 2012 | Wolviston |
| 2013 | Redcar |
| 2014 | Richmondshire |
| 2015 | Normanby Hall |
| 2016 | Richmondshire |
| 2017 | Normanby Hall |
| 2018 | Richmondshire |
| 2019 | Richmondshire |
| 2020 | Normanby Hall |
| 2021 | Wolviston |
| 2022 | Hartlepool |
| 2023 | Richmondshire |
| 2024 | Wolviston |
| 2025 | Hartlepool |
|
| Number of Wins | Club |
| 7 | Hartlepool |
| 7 | Middlesbrough |
| 6 | Normanby Hall |
| 5 | Richmondshire |
| 4 | Redcar |
| 3 | Marske |
| 3 | Wolviston |
| 2 | Stockton |
| 2 | Thornaby |
| 1 | Darlington RA |
| 1 | Norton |
|