| Season | Club |
| 1969 | Seaton Carew |
| 1970 | Castle Eden |
| 1971 | Preston |
| 1972 | Castle Eden |
| 1973 | Great Ayton |
| 1974 | Great Ayton |
| 1975 | Hartlepool |
| 1976 | Seaton Carew |
| 1977 | Seaton Carew |
| 1978 | Yarm |
| 1979 | Hartlepool |
| 1980 | Hartlepool |
| 1981 | Hartlepool |
| 1982 | Seaton Carew |
| 1983 | Darlington |
| 1984 | Marton |
| 1985 | Hartlepool |
| 1986 | Stockton |
| 1987 | Stockton |
| 1988 | Richmondshire |
| 1989 | Seaton Carew |
| 1990 | Stokesley |
| 1991 | Stokesley |
| 1992 | Hartlepool |
| 1993 | Stockton |
| 1994 | Stockton |
| 1995 | Stokesley |
| 1996 | Stockton |
| 1997 | Marton |
| 1998 | Guisborough |
| 1999 | Stockton |
| 2000 | Middlesbrough |
| 2001 | Guisborough |
| 2002 | Seaton Carew |
| 2003 | Billingham Synthonia |
| 2004 | Seaton Carew |
| 2005 | Great Ayton |
| 2006 | Billingham Synthonia |
| 2007 | |
| 2008 | |
| 2009 | Blackhall |
| 2010 | Maltby |
| 2011 | Preston |
| 2012 | Wolviston |
| 2013 | Saltburn |
| 2014 | Norton |
| 2015 | Shildon |
| 2016 | Rockcliffe Park |
| 2017 | Rockcliffe Park |
| 2018 | Normanby Hall |
| 2019 | Stockton |
| 2020 | Redcar |
| 2021 | Richmondshire |
| 2022 | Shildon Railway |
| 2023 | Normanby Hall |
| 2024 | Stokesley |
|
| Number of Wins | Club |
| 7 | Seaton Carew |
| 7 | Stockton |
| 6 | Hartlepool |
| 4 | Stokesley |
| 3 | Great Ayton |
| 2 | Billingham Synthonia |
| 2 | Castle Eden |
| 2 | Guisborough |
| 2 | Marton |
| 2 | Normanby Hall |
| 2 | Preston |
| 2 | Richmondshire |
| 2 | Rockcliffe Park |
| 1 | Blackhall |
| 1 | Darlington |
| 1 | Maltby |
| 1 | Middlesbrough |
| 1 | Norton |
| 1 | Redcar |
| 1 | Saltburn |
| 1 | Shildon |
| 1 | Shildon Railway |
| 1 | Wolviston |
| 1 | Yarm |
| 0 | |
|