| New South Wales Sydney Cup Winners | |||
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| Year | Winners | Score | Losing Finalists |
| 1940 | Metters | 4:3 | Leichhardt-Annandale |
| 1941 | |||
| 1942 | Corrimal Rangers | 5:4 | Gladesville-Ryda |
| 1943 | Leichhardt-Annandale | 9:4 | Grace Brothers |
| 1944 | Woonona-Bulli | 6:3 | Metters |
| 1945 | Woonona-Bulli | 5:2 | Metters |
| 1946 | Canterbury-Bankstown | 3:3 2:1 | Leichhardt-Annandale |
| 1947 | Woonona-Bulli | 1:0 1:1 | Corrimal Rangers |
| 1948 | Granville | 7:1 | Concord |
| 1949 | Not completed | ||
| 1950 | Metters-Campbelltown | 3:2 | Bankstown |
| 1951 | Auburn | 7:0 | Granville |
| 1952 | Leichhardt-Annandale | 3:1 | Granville |
| 1953 | Auburn | 2:1 | Granville |
| 1954 | Corrimal Rangers | 6:2 | Woonona-Bulli |
| 1955 | Corrimal Rangers | 3:1 | Auburn |
| 1956 | Leichhardt-Annandale | 2:0 | Canterbury-Marrickville |
| 1957 | Balgownie Rangers | 1:0 | Granville |
| 1958 | Balgownie Rangers | 4:0 | Leichhardt-Annandale |
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