The Caledonian Cup was competed for annually in Montreal from 1905 to 1941. For many years winning the cup was symbolic of being recognized as being the city champions. It was seen as the blue ribbon cup of Montreal.

The cup was donated to the Caledonian Society of Montreal by Peter Lyall. The proceeds of the matches was awarded to the society.

For many years the P.Q.F.A. annually nominated the team to play the holders. In the 1930’s it was the oldest local soccer trophy still played for in Montreal.

1905 Westmount
1906 Point St. Charles
1907 Westmount
1908 Rosemount
1909 M.A.A.A.
1910 Sons of Scotland
1911 Sons of Scotland
1912 Sons of Scotland
1913 Fairmount
1914 Fairmount
1915 M.A.A.A.
1916 Canadian Vickers
1917 Lyalls
1918 Canadian National
1919 Canadian National
1920 Canadian National
1921 Canadian National
1922 Canadian National
1923 Sons of Scotland
1924 Sons of Scotland
1925 Sons of Scotland
1926 Gurney and Carsteel (jointly)
1927 Carsteel
1928 Carsteel
1929 Carsteel
1930 Carsteel
1931 Maisonneuve
1932 Maisonneuve
1933 Verdun Park
1934 Hamilton United
1935 Emard St. Paul 
1936 Emard St. Paul
1937 Maisonneuve Rovers
1938 Maisonneuve Rovers
1939 Royal Victoria Hospital 
1940 Stelco
1941 Stelco