| 1919 | Lilydale |
| 1920 | Healesville |
| 1921 | Yarra Glen |
| 1922 | Lilydale |
| 1923 | Lilydale |
| 1924 | Lilydale |
| 1925 | Millgrove |
| 1926 | Croydon |
| 1927 | Little Yarra Rovers |
| 1928 | Millgrove |
| 1929 | Yarra Junction |
| 1930 | Millgrove |
| 1931 | Yarra Junction |
| 1932 | Millgrove |
| 1933 | Warburton |
| 1934 | Yarra Junction |
| 1935 | Yarra Junction |
| 1936 | Lilydale |
| 1937 | Warburton |
| 1938 | Lilydale |
| 1939 | Millgrove |
| 1940 | Millgrove |
| 1941 | Yarra Junction |
| 1942 | Suspended due to War |
| 1943 | Suspended due to War |
| 1944 | Suspended due to War |
| 1945 | Healesville |
| 1946 | Lilydale |
| 1947 | Woori Yallock |
| 1948 | Warburton |
| 1st 18 | 2nd 18 | |
| 1949 | Warburton | Healesville |
| 1950 | Yarra Junction | Healesville |
| 1951 | Healesville | Powelltown |
| 1952 | Warburton | Powelltown |
| 1953 | Warburton | Seville |
| 1954 | Healesville | Yarra Junction |
| 1955 | Yarraburn | Warburton |
| 1956 | Millgrove | Marysville |
| 1957 | Millgrove | Healesville |
| 1958 | Warburton | Lilydale |
| 1959 | Marysville | Healesville |
| 1960 | Marysville | Lilydale or Valley United |
| 1961 | Millgrove | Powelltown |
| 1962 | Healesville | Valley United |
| 1963 | Millgrove | Healesville |
| 1964 | Healesville | Powelltown |
| 1965 | Healesville |