| 1896 | Dundee Victoria |
| Arbroath United Second XI | |
| 1897 | Bowbridge |
| 1898 | Victoria |
| 1899 | Victoria |
| 1900 | Dundee Union |
| 1901 | Bowbridge |
| 1902 | Dundee Union |
| 1903 | Bowbridge |
| 1904 | Clinton Bank |
| 1905 | Woodside (Perth) |
| 1906 | Woodside (Perth) |
| 1907 | Woodside (Perth) |
| 1908 | Woodside (Perth) |
| 1909 | Woodside (Perth) |
| 1910 | Woodside (Perth) |
| 1911 | Woodside (Perth) |
| 1912 | Woodside (Perth) |
| 1913 | Woodside (Perth) |
| 1914 | Competition abandoned |
| 1915-1921 | no competition |
| 1922 | Tulloch (Perth) |
| 1923 | Tulloch (Perth) |
| 1924 | Tulloch (Perth) |
| 1925 | Tulloch (Perth) |
| 1926 | Elmwood |
| 1927 | Elmwood |
| 1928 | Strathearn (Perth) |
Alan Veitch