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1897 Peel AFC
1898 Douglas Gymnasium
1899 Ramsey FC
1900 Ramsey FC
1901 Ramsey FC
1902 Ramsey FC
1903 Douglas Gymnasium
1904 Douglas Gymnasium
1905 Douglas Gymnasium
1906 Douglas Gymnasium
1907 Peel AFC
1908 Ramsey FC
1909 Douglas Wanderers
1910 Douglas Wanderers
1911 Ramsey FC
1912 Ramsey FC
1913 Ramsey FC
1914 Castletown FC
1915 * * *
1916 * * *
1917 * * *
1918 * * *
1919 * * *
1920 Douglas Gymnasium
1921 Ramsey FC
1922 Peel AFC
1923 Castletown FC
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1924 Castletown FC
1925 Castletown FC
1926 Rushen United
1927 Ramsey FC
1928 Colby
1929 St. Marys AFC
1930 Braddan
1931 Braddan
1932 Peel AFC
1933 Peel AFC
1934 Peel AFC
1935 Peel AFC
1936 Rushen United
1937 Braddan
1938 Braddan
1939 * * *
1940 * * *
1941 * * *
1942 * * *
1943 * * *
1944 * * *
1945 * * *
1946 * * *
1947 Onchan
1948 Peel AFC
1949 Peel AFC
1950 Castletown FC
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