Orange County Titles (1895-1922)

1899 - 1902 - 1903 - 1905 - 1906 - 1907 - 1908 - 1910 - 1911 - 1912 - 1913 - 1914 - 1916 - 1917 - 1919 - 1921 - 1922

D.U.S.O. Titles (1923-1969)

1930 - 1931 - 1935 - 1936 - 1940 - 1942 - 1944 - 1954 - 1961 - 1962 - 1964 - 1965 - 1966 - 1967

(From 1970-1972 Middletown played an Independent schedule)

Orange County League (1973-1983)

Section IX Titles (1984-Present)

1993 (Class A) - 1994 (Class A)