The cup was first played for in 1914. The purpose of the cup was to provide funds for local hospitals in Montreal.
| Year | Winners |
| 1914 | Invicta |
| 1915 | Invicta |
| 1916 | Lyells |
| 1917 | Lyells |
| 1918 | Lyells |
| 1919 | Canadian National |
| 1920 | Canadian Vickers |
| 1921 | Sons of Scotland |
| 1922 | Canadian Explosives |
| 1923 | Canadian Explosives |
| 1924 | Canadian Explosives |
| 1925 | Royal Highlanders |
| 1926 | C.P.R. |
| 1927 | Carsteel |
| 1928 | Canadian National |
| 1929 | Canadian National |
| 1930 | C.P.R. |
| 1931 | C.P.R. |
| 1932 |
National Soccer League 