| Season | Club |
| 1920 | Norton |
| 1921 | Darlington |
| 1922 | Guisborough |
| 1923 | Guisborough |
| 1924 | Darlington |
| 1925 | Darlington |
| 1926 | Darlington RA |
| 1927 | Middlesbrough |
| 1928 | West Hartlepool |
| 1929 | Redcar |
| 1930 | Redcar |
| 1931 | Redcar |
| 1932 | West Hartlepool |
| 1933 | Blackhall |
| 1934 | West Hartlepool |
| 1935 | Darlington RA |
| 1936 | Middlesbrough |
| 1937 | Norton |
| 1938 | Norton |
| 1939 | Blackhall |
| 1940 | Darlington RA |
| 1941 | West Hartlepool |
| 1942 | Stockton |
| 1943 | Thornaby |
| 1944 | Thornaby |
| 1945 | Middlesbrough |
| 1946 | Norton |
| 1947 | Norton |
| 1948 | Guisborough |
| 1949 | Billingham Synthonia |
| 1950 | Darlington |
| 1951 | Darlington |
| 1952 | Middlesbrough |
| 1953 | Bishop Auckland |
| 1954 | Bishop Auckland |
| 1955 | Middlesbrough |
| 1956 | Darlington |
| 1957 | Normanby Hall |
| 1958 | Redcar |
| 1959 | Middlesbrough |
| 1960 | Blackhall |
| 1961 | Middlesbrough |
| 1962 | Billingham Synthonia |
| 1963 | Darlington |
| 1964 | Norton |
| 1965 | Guisborough |
| 1966 | Billingham Synthonia |
| 1967 | Saltburn |
| 1968 | Middlesbrough |
| 1969 | Hartlepool |
| 1970 | Guisborough |
| 1971 | Saltburn |
| 1972 | Normanby Hall |
| 1973 | Darlington RA |
| 1974 | Bishop Auckland |
| 1975 | Northallerton |
| 1976 | Middlesbrough |
| 1977 | Normanby Hall |
| 1978 | Darlington |
| 1979 | Hartlepool |
| 1980 | Bishop Auckland |
| 1981 | Bishop Auckland |
| 1982 | Guisborough |
| 1983 | Guisborough |
| 1984 | Normanby Hall |
| 1985 | Norton |
| 1986 | Middlesbrough |
| 1987 | Darlington RA |
| 1988 | Hartlepool |
| 1989 | Middlesbrough |
| 1990 | Redcar |
| 1991 | Hartlepool |
| 1992 | Bishop Auckland |
| 1993 | Darlington |
| 1994 | Middlesbrough |
| 1995 | Normanby Hall |
| 1996 | Darlington |
| 1997 | Darlington |
| 1998 | Darlington RA |
| 1999 | Normanby Hall |
| 2000 | Middlesbrough |
| 2001 | Middlesbrough |
| 2002 | Middlesbrough |
| 2003 | Saltburn |
| 2004 | Guisborough |
| 2005 | Saltburn |
| 2006 | Guisborough |
| 2007 | Middlesbrough |
| 2008 | Middlesbrough |
| 2009 | Marton |
| 2010 | Stokesley |
| 2011 | Marton |
| 2012 | Marton |
| 2013 | Marton |
| 2014 | Barnard Castle |
| 2015 | Great Ayton |
| 2016 | Barnard Castle |
| 2017 | Richmondshire |
| 2018 | Richmondshire |
| 2019 | Barnard Castle |
| 2020 | Richmondshire |
| 2021 | Hartlepool |
| 2022 | Richmondshire |
| 2023 | Marton |
| 2024 | Barnard Castle |
| 2025 | Baranrd Castle |
|
| Number of Wins | Club |
| 17 | Middlesbrough |
| 11 | Darlington |
| 9 | Guisborough |
| 7 | Norton |
| 6 | Bishop Auckland |
| 6 | Darlington RA |
| 6 | Normanby Hall |
| 5 | Hartlepool |
| 5 | Marton |
| 5 | Redcar |
| 4 | Barnard Castle |
| 4 | Richmondshire |
| 4 | Saltburn |
| 4 | West Hartlepool |
| 3 | Billingham Synthonia |
| 3 | Blackhall |
| 2 | Thornaby |
| 1 | Baranrd Castle |
| 1 | Great Ayton |
| 1 | Northallerton |
| 1 | Stockton |
| 1 | Stokesley |
|