Cup Winners

Year	Club
1897	Norton
1898	Norton
1899	Norton
1900	Darlington
1901	Darlington
1902	Darlington
1903	Preston
1904	Stockton
1905	West Hartlepool
1906	Stockton
1907	Darlington
1908	Darlington
1909	Redcar
1910	Redcar
1911	Darlington
1912	Stockton
1913	Stockton
1914	Stockton
1920	Darlington
1921	Darlington
1922	Preston
1923	Darlington
1924	Darlington
1925	Bishop Auckland
1926	Darlington
1927	Darlington
1928	Stockton
1929	Darlington
1930	Thornaby
1931	Middlesbrough
1932	West Hartlepool
1933	Yarm
1934	Guisborough
1935	Guisborough
1936	Marton
1937	West Hartlepool
1938	Marton
1939	West Hartlepool
1941	Preston
1942	Darlington
1943	Preston
1944	Summersons
1945	Mainsforth
1946	Stockton
1947	Preston
1948	Preston
1949	Darlington
1950	Darlington
1951	Darlington RA
1952	Darlington
1953	Darlington
1954	Thornaby
1955	West Hartlepool
1956	Billingham Synthonia
1957	Stockton
1958	Blackhall
1959	Darlington
1960	Middlesbrough
1961	Darlington
1962	Barnard Castle
1963	Marske
1964	Middlesbrough
1965	Marske
1966	Middlesbrough
1967	Barnard Castle
1968	Seaton Carew
1969	Great Ayton
1970	Marske
1971	Barnard Castle
1972	Great Ayton
1973	Yarm
1974	Stockton
1975	Barnard Castle
1976	Stockton
1977	Great Ayton
1978	Great Ayton
1979	Great Ayton
1980	Great Ayton
1981	Seaton Carew
1982	Richmondshire
1983	Richmondshire
1984	Stokesley
1985	Richmondshire
1986	Seaton Carew
1987	Thornaby
1988	Marton
1989	Stokesley
1990	Richmondshire
1991	Richmondshire
1992	Marske
1993	Stockton
1994	Billingham Synthonia
1995	Barnard Castle
1996	Marton
1997	Wolviston
1998	Richmondshire
1999	Thornaby
2000	Barnard Castle
2001	Wolviston
2002	Bishop Auckland
2003	Great Ayton
2004	Billingham Synthonia
2005	Marton
2006	Blackhall
2007	Billingham Synthonia
2008	Thornaby
2009	Stokesley
2010	Barnard Castle
2011	Sedgefield
2012	Saltburn
2013	Marske
2014	Norton
2015	Billingham Synthonia
2016	Marton
2017	Thornaby
2018	Billingham Synthonia
2019	Saltburn
2020	Stockton
2021	Stockton
2022	Bishop Auckland
2023	Marton