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1896 Gibraltar FC
1897 Jubilee FC
1898 Jubilee FC
1899 Albion FC
1900 Exiles FC
1901 Prince of Wales FC
1902 Exiles FC
1903 Prince of Wales FC
1904 Prince of Wales FC
1905 Athletic FC
1906 Prince of Wales FC
1907 * * *
1908 Britannia FC
1909 Prince of Wales FC
1910 South United FC
1911 South United FC
1912 Britannia FC
1913 Britannia FC
1914 Prince of Wales FC
1915 Royal Sovereign
1916 * * *
1917 Prince of Wales FC
1918 Britannia FC
1919 Prince of Wales FC
1920 Britannia FC
1921 Prince of Wales FC
1922 Prince of Wales FC
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1923 Prince of Wales FC
1924 Gibraltar FC
1925 Prince of Wales FC
1926 Prince of Wales FC
1927 Prince of Wales FC
1928 Prince of Wales FC
1929 Europa FC
1930 Europa FC
1931 Prince of Wales FC
1932 Europa FC
1933 Europa FC
1934 Commander of the Yard FC
1935 Chief Construction FC
1936 Chief Construction FC
1937 Britannia FC
1938 Europa FC
1939 Prince of Wales FC
1940 Prince of Wales FC
1941 Britannia FC
1942 * * *
1943 * * *
1944 * * *
1945 * * *
1946 * * *
1947 Gibraltar United FC
1948 Gibraltar United FC
1949 Gibraltar United FC
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