| Season | Club |
| 1946 | Billingham Synthonia |
| 1947 | Blackhall |
| 1948 | West Hartlepool |
| 1949 | Great Ayton |
| 1950 | Marton |
| 1951 | Normanby Hall |
| 1952 | Guisborough |
| 1953 | Thornaby |
| 1954 | Norton |
| 1955 | Marton |
| 1956 | Norton |
| 1957 | Darlington |
| 1958 | Marton |
| 1959 | Darlington |
| 1960 | Darlington |
| 1961 | Marton |
| 1962 | Bishop Auckland |
| 1963 | Middlesbrough |
| 1964 | Great Ayton |
| 1965 | Marske |
| 1966 | Middlesbrough |
| 1967 | Great Ayton |
| 1968 | Seaton Carew |
| 1969 | Norton |
| 1970 | Barnard Castle |
| 1971 | Yarm |
| 1972 | Great Ayton |
| 1973 | Castle Eden |
| 1974 | Darlington |
| 1975 | Norton |
| 1976 | Northallerton |
| 1977 | Great Ayton |
| 1978 | Blackhall |
| 1979 | Seaton Carew |
| 1980 | Seaton Carew |
| 1981 | Stockton |
| 1982 | Marton |
| 1983 | Richmondshire |
| 1984 | Richmondshire |
| 1985 | Saltburn |
| 1986 | Seaton Carew |
| 1987 | Marton |
| 1988 | Billingham Synthonia |
| 1989 | Richmondshire |
| 1990 | Richmondshire |
| 1991 | Preston |
| 1992 | Norton |
| 1993 | Stokesley |
| 1994 | Billingham Synthonia |
| 1995 | Marske |
| 1996 | Marton |
| 1997 | Marton |
| 1998 | Richmondshire |
| 1999 | Guisborough |
| 2000 | Billingham Synthonia |
| 2001 | Wolviston |
| 2002 | Bishop Auckland |
| 2003 | Great Ayton |
| 2004 | Thornaby |
| 2005 | Marton |
| 2006 | Normanby Hall |
| 2007 | Middlesbrough |
| 2008 | Saltburn |
| 2009 | Stokesley |
| 2010 | Darlington |
| 2011 | Sedgefield |
| 2012 | Bishop Auckland |
| 2013 | Bishop Auckland |
| 2014 | Normanby Hall |
| 2015 | Billingham Synthonia |
| 2016 | Marton |
| 2017 | Saltburn |
| 2018 | Saltburn |
| 2019 | Bishop Auckland |
| 2020 | Darlington |
| 2021 | Middlesbrough |
| 2022 | Bishop Auckland |
| 2023 | Normanby Hall |
| 2024 | Billingham Synthonia |
| 2025 | Billingham Synthonia |
|
| Number of Wins | Club |
| 10 | Marton |
| 7 | Billingham Synthonia |
| 6 | Bishop Auckland |
| 6 | Darlington |
| 6 | Great Ayton |
| 5 | Norton |
| 5 | Richmondshire |
| 4 | Middlesbrough |
| 4 | Normanby Hall |
| 4 | Saltburn |
| 4 | Seaton Carew |
| 2 | Blackhall |
| 2 | Guisborough |
| 2 | Marske |
| 2 | Stokesley |
| 2 | Thornaby |
| 1 | Barnard Castle |
| 1 | Castle Eden |
| 1 | Northallerton |
| 1 | Preston |
| 1 | Sedgefield |
| 1 | Stockton |
| 1 | West Hartlepool |
| 1 | Wolviston |
| 1 | Yarm |
|