| 1893 | Constable Burton |
| 1894 | Redcar |
| 1895 | Guisborough |
| 1896 | Darlington |
| 1897 | Stockton |
| 1898 | Norton |
| 1899 | West Hartlepool |
| 1900 | West Hartlepool |
| 1901 | West Hartlepool |
| 1902 | Norton |
| 1903 | Norton |
| 1904 | Darlington |
| 1905 | Guisborough |
| 1906 | Darlington |
| 1907 | Guisborough |
| 1908 | West Hartlepool |
| 1909 | Guisborough |
| 1910 | Guisborough |
| 1911 | Guisborough |
| 1912 | Guisborough |
| 1913 | West Hartlepool |
| 1914 | Norton |
| 1915-1918 | No competition |
| 1919 | Middlesbrough |
| 1920 | Darlington |
| 1921 | Darlington |
| 1922 | Darlington |
| 1923 | Darlington |
| 1924 | Redcar |
| 1925 | Darlington |
| 1926 | Darlington |
| 1927 | Redcar |
| 1928 | West Hartlepool |
| 1929 | Darlington Railway Athletic |
| 1930 | Darlington |
| 1931 | Redcar |
| 1932 | Darlington Railway Athletic |
| 1933 | Blackhall |
| 1934 | Bishop Auckland |
| 1935 | Norton |
| 1936 | Blackhall |
| 1937 | Norton |
| 1938 | Norton |
| 1939 | Blackhall |
| 1940 | Normanby Hall |
| 1941 | Darlington |
| 1942 | Guisborough |
| 1943 | Thornaby |
| 1944 | Darlington Railway Athletic |
| 1945 | Thornaby |
| 1946 | Norton |
| 1947 | Normanby Hall |
| 1948 | Stockton |
| 1949 | Norton |
| 1950 | Darlington |
| 1951 | Norton |
| 1952 | Redcar |
| 1953 | Darlington |
| 1954 | Darlington |
| 1955 | Darlington |
| 1956 | Normanby Hall |
| 1957 | Middlesbrough |
| 1958 | Darlington |
| 1959 | Middlesbrough |
| 1960 | Middlesbrough |
| 1961 | Middlesbrough |
| 1962 | Darlington |
| 1963 | Normanby Hall |
| 1964 | West Hartlepool |
| 1965 | Redcar |
| 1966 | Bishop Auckland |
| 1967 | Saltburn |
| 1968 | Saltburn |
| 1969 | Saltburn |
| 1970 | Middlesbrough |
| 1971 | Marske |
| 1972 | Guisborough |
| 1973 | Bishop Auckland |
| 1974 | Saltburn |
| 1975 | Stockton |
| 1976 | Guisborough |
| 1977 | Darlington |
| 1978 | Hartlepool |
| 1979 | Saltburn |
| 1980 | Bishop Auckland |
| 1981 | Guisborough |
| 1982 | Hartlepool |
| 1983 | Billingham Synthonia |
| 1984 | Marske |
| 1985 | Darlington |
| 1986 | Thornaby |
| 1987 | Darlington |
| 1988 | Hartlepool |
| 1989 | Guisborough |
| 1990 | Darlington |
| 1991 | Redcar |
| 1992 | Redcar |
| 1993 | Middlesbrough |
| 1994 | Middlesbrough |
| 1995 | Richmondshire |
| 1996 | Guisborough |
| 1997 | Normanby Hall |
| 1998 | Norton |
| 1999 | Bishop Auckland |
| 2000 | Saltburn |
| 2001 | Guisborough |
| 2002 | Guisborough |
| 2003 | Guisborough |
| 2004 | Guisborough |
| 2005 | Saltburn |
| 2006 | Great Ayton |
| 2007 | Middlesbrough |
| 2008 | Middlesbrough |
| 2009 | Marton |
| 2010 | Middlesbrough |
| 2011 | Marton |
| 2012 | Richmondshire |
| 2013 | Richmondshire |
| 2014 | Darlington |
| 2015 | Richmondshire |
| 2016 | Barnard Castle |
| 2017 | Great Ayton |
| 2018 | Barnard Castle |
| 2019 | Richmondshire |
| 2020 | No competition |
| 2021 | Richmondshire |
| 2022 | Middlesbrough |
| 2023 | Saltburn |
| 2024 | Richmondshire |
| 2025 | Barnard Castle |
Peter Hartland
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