| New South Wales Cup Winners | |||
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| Rainsford Trophy | |||
| Year | Winners | Score | Losing Finalists |
| 1885 | Granville | 3:1 aet | Caledonian |
| 1886 | Granville | 2:0 | Canterbury |
| 1887 | Hamilton Athletic | 4:1 | Granville |
| Gardiner Challenge Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1888 | Caledonian | 4:2 | Parkgrove |
| 1889 | Pyrmont Rangers | 1-0 | Joadga |
| 1890 | Pyrmont Rangers | 3:1 | Granville |
| 1891 | Parkgrove | 4:1 | Pyrmont Rangers |
| 1892 | Minmi Rangers | 3-0 | Pyrmont Rangers |
| 1893 | Pyrmont Rangers | 1-0 | Minmi Rangers |
| 1894 | Pyrmont Rangers | 7:2 | Parkgrove |
| 1895 | Balmain | 4:2 | Pyrmont Rangers |
| 1896 | Balmain | 3:1 | Pyrmont Rangers |
| 1897 | Balmain | 2:1 | Pyrmont Rangers |
| 1898 | Volunteer | 3:2 | West Newcastle |
| 1899 | Pyrmont Rangers | 5:2 | Balgownie |
| 1900 | West Wallsend | 3:3 4:1 | Volunteers |
| 1901 | West Wallsend | 4:1 | Balgownie |
| 1902 | Pyrmont Rovers | 3:1 | West Wallsend |
| 1903 | Pyrmont District | 4:2 | Glebe |
| 1904 | Granville | 2:1 | Glebe |
| 1905 | Balmain | 2:2 2:1 | Rozelle |
| 1906 | Glebe | 3:2 | Pyrmont |
| 1907 | Broadmeadow | 0:0 3:2 | Pyrmont |
| 1908 | Pyrmont | 4-0 | Glebe |
| 1909 | Adamstown | 0:0 3:1 | Pyrmont Rovers |
| 1910 | HMS Powerful | 2-0 | Helensburgh FC |
| 1911 | Balmain | 2:1 | HMS Powerful |
| 1912 | Balmain | 1-0 | Sydney FC |
| 1913 | Annandale | 3-0 | Newtown |
| 1914 | Granville | 3:1 | Merewether |
| 1915 | Balmain | 2-0 | West Wallsend |
| 1916 | No Competition | ||
| 1917 | No Competition | ||
| 1918 | Weston United | 1-0 | Balmain Kiora |
| 1919 | Balmain Fernleigh | 3-0 | West Wallsend |
| 1920 | Balmain Fernleigh | 2-0 | Granville |
| 1921 | West Wallsend | 3:1 | Granville |
| 1922 | Granville | 1-0 | West Wallsend |
| 1923 | West Wallsend | 0:0 0:0 4:4 1-0 | Sydney FC |
| 1924 | West Wallsend | 3-0 | Woonona |
| 1925 | Adamstown | 2-0 | Cessnock |
| 1926 | West Wallsend | 2:1 | Adamstown |
| 1927 | Gladesville-Ryde | 2-0 | Granville |
| 1928 | Thirroul Rangers | 3-0 | Pyrmont |
| New South Wales State Cup Series | |||
| Year | Winners | Score | Losing Finalists |
| 1928 | Aberdare | 2-0 | Weston |
| 1929 | Cessnock | 5:2 | Wallsend |
| 1930 | Adamstown | 2-0 | Cessnock |
| 1931 | West Wallsend | 3-0 | Woonona |
| 1932 | Weston | 8:1 | Adamstown |
| 1933 | St. George | 3:3 5:3 | Cessnock |
| 1934 | Weston | 5:1 | Adamstown |
| 1935 | Metters | 5-0 | St. George |
| 1936 | Weston | 3:2 | Metters |
| 1937 | Wallsend | 3:1 | Weston |
| 1938 | Metters | 4-0 | Adamstown |
| 1939 | Weston | 2:2 2:1 | Goodyear |
| 1940 | Metters | 4:2 | Adamstown |
| 1941 | Leichhardt-Annandale | 6:3 | Granville |
| 1942 | Wallsend | 8:1 | Gladesville-Ryde |
| 1943 | Merewether | 4:2 | Woonona-Bulli |
| 1944 | Merewether | 6:3 | Cessnock |
| New South Wales State League Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1943 | Leichhardt-Annandale | 3:2 aet | Adamstown |
| 1944 | Wallsend | 8:2 | Grace Brothers |
| 1945 | West Wallsend | 2:1 | Metters |
| 1946 | Canterbury-Bankstown | 4:1 | Adamstown |
| 1947 | Corrimal Rangers | 5:1 | Canterbury-Bankstown |
| 1948 | Leichhardt-Annandale | 4:2 | Wallsend |
| 1949 | Leichhardt-Annandale | 3-0 | Granville |
| 1950 | Wallsend | 5:2 | Granville |
| 1951 | Granville | 3-0 | Mayfield United |
| 1952 | Wallsend | 2-0 | West Wallsend |
| 1953 | Auburn | 1-0 | Corrimal |
| 1954 | Corrimal Rangers | 5:1 | Leichhardt-Annandale |
| 1955 | Leichhardt-Annandale | 2:1 | Granville |
| 1956 | Leichhardt-Annandale | 6:4 | Corrimal Rangers |
| 1957 | Wallsend | 0:0 2-0 | Granville |
| 1958 | Toronto-Awaba | 4:2 | Wallsend |
| Federation Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1957 | Canterbury Marrickville | 7:2 | Gladesville-Ryde |
| 1958 | Canterbury Marrickville | 3:2 | Prague |
| Ascot (Craven) Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1959 | Hakoah | 2:0 | Prague |
| 1960 | Bankstown | 1:0 | Canterbury Marrickville |
| 1961 | Hakoah | 2:0 | Canterbury Marrickville |
| Federation Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1962 | A.P.I.A. Leichhardt | 5:1 | Canterbury Marrickville |
| 1963 | Hakoah Eastern Suburbs | 2:1 | South Coast United |
| 1964 | St. George Budapest | 4:3 | South Coast United |
| 1965 | Hakoah Eastern Suburbs | 3:1 | Pan-Hellenic |
| 1966 | A.P.I.A. Leichhardt | 3:2 | St. George Budapest |
| 1967-1970 | No Competition | ||
| 1971 | Hakoah Eastern Suburbs | 3:2 | South Sydney-Croatia |
| 1972 | St. George Budapest | 3:2 | Marconi Fairfield |
| 1973 | No Competition | ||
| 1974 | South Sydney-Croatia | 1:0 | St. George Budapest |
| 1975 | A.P.I.A. Leichhardt | 2:0 | Western Suburbs |
| 1976 | Hakoah Eastern Suburbs | 3:1 | South Sydney-Croatia |
| 1977-1990 | No Competition | ||
| 1990 | Canberra Croatia | 3:0 | Sydney Macedonia |
| Waratah Cup | |||
| Year | Winners | Score | Losing Finalists |
| 1991 | Blacktown City | 2:1 | Avala |
| 1992 | Avala | 4:1 | Canberra Metro |
| 1993 | Blacktown City | ||
| 1994 | Bankstown City | 2:1 | Sydney Olympic |
| 1995 | Sydney United | 2:1 | Canterbury Marrickville |
| 1996 | Sydney United | 2:1 aet | Parramatta Eagles |
| 1997 | Wollongong Wolves | 2:0 | Bankstown City |
| Statewide Cup | |||
| Year | Winners | Score | Losing Finalists |
| 2004 | Sydney Crescent Stars | 2:1 aet | Bonnyrigg White Eagles |
| 2005 | Sydney United | 3:1 | Belconnen Blue Devils |
| 2006 | Blacktown City | 2:1 | A.P.I.A. Leichhardt |
| 2007 | Wollongong Wolves | 3:2 | Manly United |
| 2008 | Bankstown City | 3:1 | Sydney Olympic |
| 2009 | Sutherland Sharks | 2:1 | Manly United |
| Waratah Cup | |||
| Year | Winners | Score | Losing Finalists |
| 2010 | Marconi Stallions | 0:0 7:6 pens | Spirit FC |
| 2011 | Manly United | 4:0 | Mounties Wanderers |
| 2012 | Sutherland Sharks | 4:1 | A.P.I.A. Leichhardt |
| 2013 | A.P.I.A. Leichhardt | 3:0 | Sutherland Sharks |
| 2014 | Blacktown City | 6:2 | Manly United |
| 2015 | Sydney United 58 | 1:0 | Blacktown City |
| 2016 | |||
| Number of Cup wins since 1957. Previous clubs names in brackets | |||
| 6 | Hakoah Sydney City East (Hakoah, Hakoah Eastern Suburbs) | ||
| 5 | Sydney United 58 (Sydney United, Croatia Sydney) | ||
| 4 | A.P.I.A. Leichhardt | ||
| 4 | Blacktown City | ||
| 3 | Bankstown City | ||
| 2 | Bankstown Berries (Canterbury Marrickville) | ||
| 2 | South Coast Wolves (Wollongong Wolves) | ||
| 2 | St. George FC (St George-Budapest) | ||
| 2 | Sutherland Sharks | ||
| 1 | Bonnyrigg White Eagles (Avala) | ||
| 1 | Canberra FC (Canberra Croatia) | ||
| 1 | Manly United | ||
| 1 | Marconi Stallions | ||
| 1 | Sydney Crescent Stars | ||
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