List of League Winners
- 1896–97: Peel
- 1897–98: Gymnasium
- 1898–99: Ramsey
- 1899–1900: Ramsey
- 1900–01: Ramsey
- 1901–02: Ramsey
- 1902–03: Gymnasium
- 1903–04: Gymnasium
- 1904–05: Gymnasium
- 1905–06: Gymnasium
- 1906–07: Peel
- 1907–08: Ramsey
- 1908–09: Douglas Wanderers
- 1909–10: Douglas Wanderers
- 1910–11: Ramsey
- 1911–12: Ramsey
- 1912–13: Ramsey
- 1913–14: Castletown Metropolitan
- 1914–15 – 1918–19 (no competition due to World War I)
- 1919–20: Gymnasium
- 1920–21: Ramsey
- 1921–22: Peel
- 1922–23: Castletown Metropolitan
- 1923–24: Castletown Metropolitan
- 1924–25: Castletown Metropolitan
- 1925–26: Rushen United
- 1926–27: Ramsey
- 1927–28: Colby
- 1928–29: St Marys
- 1929–30: Braddan
- 1930–31: Braddan
- 1931–32: Peel
- 1932–33: Peel
- 1933–34: Peel
- 1934–35: Peel
- 1935–36: Rushen United
- 1936–37: Braddan
- 1937–38: Braddan
- 1938–39 – 1945–46 (no competition due to World War II)
- 1946–47: Onchan
- 1947–48: Peel
- 1948–49: Peel
- 1949–50: Castletown Metropolitan
- 1950–51: Castletown Metropolitan
- 1951–52: Ramsey
- 1952–53: Peel
- 1953–54: Peel
- 1954–55: Peel
- 1955–56: RAF Jurby
- 1956–57: St Georges
- 1957–58: Peel
- 1958–59: Peel
- 1959–60: Peel
- 1960–61: St Georges
- 1961–62: St Georges
- 1962–63: Peel
- 1963–64: Peel
- 1964–65: Peel
- 1965–66: Peel
- 1966–67: Douglas High School Old Boys
- 1967–68: Pulrose United
- 1968–69: Pulrose United
- 1969–70: Pulrose United
- 1970–71: Pulrose United
- 1971–72: Peel
- 1972–73: Peel
- 1973–74: Peel
- 1974–75: Peel
- 1975–76: Peel
- 1976–77: Peel
- 1977–78: Rushen United
- 1978–79: Rushen United
- 1979–80: Rushen United
- 1980–81: Rushen United
- 1981–82: Castletown Metropolitan
- 1982–83: Douglas High School Old Boys
- 1983–84: Peel
- 1984–85: Rushen United
- 1985–86: Rushen United
- 1986–87: Gymnasium
- 1987–88: Rushen United
- 1988–89: Douglas High School Old Boys
- 1989–90: Douglas High School Old Boys
- 1990–91: Douglas High School Old Boys
- 1991–92: St Georges
- 1992–93: Pulrose United
- 1993–94: St Georges
- 1994–95: St Georges
- 1995–96: St Marys
- 1996–97: Douglas High School Old Boys
- 1997–98: St Marys
- 1998–99: Castletown Metropolitan
- 1999–2000: Peel
- 2000–01: Peel
- 2001–02: Peel
- 2002–03: St Marys
- 2003–04: St Georges
- 2004–05: St Georges
- 2005–06: Laxey
- 2006–07: St Georges
- 2007–08: St Georges
- 2008–09: St Georges
- 2009–10: Rushen United
- 2010–11: St Georges
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—Kurt Vonnegut, Jr. (b. 1922)