| Year | Grade | Premiers | Comment |
| 1874 | 1st Grade | Waratah | |
| 1875 | 1st Grade | Balmain | |
| 1876 | 1st Grade | Wallaroo | |
| 1877 | 1st Grade | Wallaroo | |
| 1878 | 1st Grade | Wallaroo | |
| 1879 | 1st Grade | Wallaroo | |
| 1880 | 1st Grade | Wallaroo | |
| 1881 | 1st Grade | Sydney University | |
| 1882 | 1st Grade | Sydney University | |
| 1883 | 1st Grade | Redfern | Gardiners Cup 1883-1889 |
| 1884 | 1st Grade | Burwood | |
| 1885 | 1st Grade | Sydney University | |
| 1886 | 1st Grade | Gordon | |
| 1887 | 1st Grade | Sydney University | |
| 1888 | 1st Grade | Sydney University | |
| 1889 | 1st Grade | Sydney University | |
| 1890 | 1st Grade | University | RAS Shield 1890-1893 |
| 1891 | 1st Grade | Sydney University | |
| 1892 | 1st Grade | Wallaroo | |
| 1893 | 1st Grade | Sydney University | |
| 1894 | 1st Grade | Randwick | Union Medal 1894-1896 |
| 1895 | 1st Grade | Randwick | |
| 1896 | 1st Grade | Randwick | |
| 1897 | 1st Grade | Randwick | Nash Cup 1897-1899 |
| 1898 | 1st Grade | Pirates | |
| 1899 | 1st Grade | Wallaroo | |
| 1900 | 1st Grade | Glebe | |
| 1900 | 2nd Grade | Glebe | |
| 1900 | 3rd Grade | Glebe | |
| 1901 | 1st Grade | Glebe & Sydney Uni** | Joint Premiers |
| 1901 | 2nd Grade | Sydney Uni 9 def Glebe 6 | Challenge Final |
| 1901 | 3rd Grade | Balmain | |
| 1902 | 1st Grade | Wests | |
| 1902 | 2nd Grade | Glebe | |
| 1903 | 1st Grade | Easts | |
| 1903 | 2nd Grade | Newtown | |
| 1904 | 1st Grade | Sydney Uni | |
| 1904 | 2nd Grade | Glebe & Sydney Uni** | Joint Premiers |
| 1905 | 1st Grade | South Sydney | |
| 1905 | 2nd Grade | Easts 3 def Glebe 0 | Challenge Final |
| 1906 | 1st Grade | Glebe | |
| 1906 | 2nd Grade | Marrickville | |
| 1907 | 1st Grade | Glebe 13 def Sydney Uni 0 | Challenge Final |
| 1907 | 2nd Grade | Newtown | |
| 1908 | 1st Grade | Newtown 17 def Sydney Uni 0 | Challenge Final |
| 1908 | 2nd Grade | Glebe 16 def Sydney Uni 0 | Challenge Final |
| 1908 | 3rd Grade | Waterloo 5 def St Peters 0 | Challenge Final |
| 1909 | 1st Grade | Glebe 17 def South Sydney 6 | Challenge Final |
| 1909 | 2nd Grade | Sydney | |
| 1909 | 3rd Grade | South Sydney 11 def St Peters 6 | Challenge Final |
| 1910 | 1st Grade | Newtown | |
| 1910 | 2nd Grade | Glebe 21 def Sydney Training College 3 | Challenge Final |
| 1910 | 3rd Grade | South Sydney 9 def Newtown 3 | Challenge Final |
| 1911 | 1st Grade | Newtown 27 def Sydney Uni 10 | Challenge Final |
| 1911 | 2nd Grade | Sydney Training College | |
| 1911 | 3rd Grade | Camperdown 11 def Balmain 5 | Challenge Final |
| 1912 | 1st Grade | Glebe 6 def Wests 5 | Challenge Final |
| 1912 | 2nd Grade | Easts 3 def Newtown 0 | Challenge Final |
| 1912 | 3rd Grade | Randwick 5 def Newtown 3 | Challenge Final |
| 1913 | 1st Grade | Easts | |
| 1913 | 2nd Grade | Easts 17 def Randwick 11 | Challenge Final |
| 1913 | 3rd Grade | Glebe*** 9 def Manly 3 | Challenge Final (*** After extra time) |
| 1914 | 1st Grade | Glebe | |
| 1914 | 2nd Grade | YMCA 20 def Randwick 11 | Challenge Final |
| 1914 | 3rd Grade | Manly* 8 Newtown 8 | *Premiers after draw in Challenge Final |
| 1919 | 1st Grade | Sydney Uni | |
| 1919 | 2nd Grade | Sydney Uni | |
| 1920 | 1st Grade | Sydney Uni | |
| 1920 | 2nd Grade | Manly | |
| 1921 | 1st Grade | Easts 9 def Manly 6 | Challenge Final |
| 1921 | 2nd Grade | Manly | |
| 1922 | 1st Grade | Manly* 6 Glebe-Balmain 6 | *Premiers after draw in Challenge Final |
| 1922 | 2nd Grade | Manly | |
| 1923 | 1st Grade | Sydney Uni 23 def Glebe-Balmain 14 | Challenge Final |
| 1923 | 2nd Grade | Manly | |
| 1924 | 1st Grade | Sydney Uni 19 def Wests 10 | Challenge Final |
| 1924 | 2nd Grade | Sydney Uni | |
| 1925 | 1st Grade | Glebe-Balmain | |
| 1925 | 2nd Grade | Norths | |
| 1926 | 1st Grade | Sydney Uni 19 def Randwick 15 | Challenge Final |
| 1926 | 2nd Grade | Manly 13 def Sydney Uni 9 | Challenge Final |
| 1927 | 1st Grade | Sydney Uni | |
| 1927 | 2nd Grade | Wests 17 def Norths 8 | Challenge Final |
| 1928 | 1st Grade | Sydney Uni 38 def YMCA 11 | Challenge Final |
| 1928 | 2nd Grade | Norths | |
| 1929 | 1st Grade | Wests 18 def Norths 9 | Challenge Final |
| 1929 | 2nd Grade | Manly 18 def Norths 14 | Challenge Final |
| 1929 | 3rd Grade | YMCA | |
| 1930 | 1st Grade | Randwick | |
| 1930 | 2nd Grade | Randwick | |
| 1930 | 3rd Grade | Manly 9 def Randwick 6 | Challenge Final |
| 1931 | 1st Grade | Easts 16 def Manly 9 | Challenge Final |
| 1931 | 2nd Grade | Norths | |
| 1931 | 3rd Grade | Wests | |