| Season | Club |
| 1973 | Stockton |
| 1974 | Stockton |
| 1975 | Normanby Hall |
| 1976 | Bishop Auckland |
| 1977 | Hartlepool |
| 1978 | Marske |
| 1979 | Marske |
| 1980 | Darlington |
| 1981 | Hartlepool |
| 1982 | Marske |
| 1983 | Norton |
| 1984 | Hartlepool |
| 1985 | Bishop Auckland |
| 1986 | Billingham Synthonia |
| 1987 | Stockton |
| 1988 | Darlington |
| 1989 | Darlington |
| 1990 | Hartlepool |
| 1991 | Hartlepool |
| 1992 | Darlington RA |
| 1993 | Darlington |
| 1994 | Middlesbrough |
| 1995 | Norton |
| 1996 | Norton |
| 1997 | Darlington |
| 1998 | Normanby Hall |
| 1999 | Guisborough |
| 2000 | Blackhall |
| 2001 | Hartelpool |
| 2002 | Thornaby |
| 2003 | Hartlepool |
| 2004 | Normanby Hall |
| 2005 | Middlesbrough |
| 2006 | Middlesbrough |
| 2007 | Middlesbrough |
| 2008 | Middlesbrough |
| 2009 | Blackhall |
| 2010 | Marton |
| 2011 | Darlington |
| 2012 | Hartlepool |
| 2013 | Great Ayton |
| 2014 | Middlesbrough |
| 2015 | Richmondshire |
| 2016 | Barnard Castle |
| 2017 | Barnard Castle |
| 2018 | Richmondshire |
| 2019 | Darlington |
| 2020 | No competition - CoronaVirus |
| 2021 | Richmondshire |
| 2022 | Great Ayton |
| 2023 | Hartlepool |
|
| Number of Wins | Club |
| 8 | Hartlepool |
| 7 | Darlington |
| 6 | Middlesbrough |
| 3 | Marske |
| 3 | Normanby Hall |
| 3 | Norton |
| 3 | Richmondshire |
| 3 | Stockton |
| 2 | Barnard Castle |
| 2 | Bishop Auckland |
| 2 | Blackhall |
| 2 | Great Ayton |
| 1 | Billingham Synthonia |
| 1 | Darlington RA |
| 1 | Guisborough |
| 1 | Hartelpool |
| 1 | Marton |
| 1 | No competition - CoronaVirus |
| 1 | Thornaby |
|