Hong Kong Challenge Shield is one of the oldest football competitions in Asia, established in 1896. It had been divided in Senior Challenge Shield and Junior Challenge Shield since 1922–23 season.
| # | Season | Winner | |
|---|---|---|---|
| — | 1895–96 | Kowloon | |
| 1 | 1896–97 | HMS Centurion | |
| 2 | 1897–98 | ||
| 3 | 1898–99 | ||
| 4 | 1899–1900 | ||
| 5 | 1900–01 | ||
| 6 | 1901–02 | ||
| 7 | 1902–03 | ||
| 8 | 1903–04 | ||
| 9 | 1904–05 | ||
| 10 | 1905–06 | ||
| 11 | 1906–07 | ||
| 12 | 1907–08 | ||
| 13 | 1908–09 | ||
| 14 | 1909–10 | ||
| 15 | 1910–11 | ||
| 16 | 1911–12 | ||
| 17 | 1912–13 | ||
| 18 | 1913–14 | ||
| 19 | 1914–15 | ||
| 20 | 1915–16 | ||
| 21 | 1918–19 | ||
| 22 | 1919–20 | ||
| 23 | 1920–21 | ||
| 24 | 1921–22 | ||
| # | Season | Senior winner | Junior winner |
| 25 | 1922–23 | ||
| 26 | 1923–24 | ||
| 27 | 1924–25 | ||
| 28 | 1925–26 | ||
| 29 | 1926–27 | ||
| 30 | 1927–28 | ||
| 31 | 1928–29 | ||
| 32 | 1929–30 | ||
| 33 | 1930–31 | ||
| 34 | 1931–32 | ||
| 35 | 1932–33 | ||
| 36 | 1933–34 | ||
| 37 | 1934–35 | ||
| 38 | 1935–36 | ||
| 39 | 1936–37 | ||
| 40 | 1937–38 | ||
| 41 | 1938–39 | ||
| 42 | 1939–40 | ||
| 43 | 1940–41 | ||
| 44 | 1945–46 | ||
| 45 | 1946–47 | ||
| 46 | 1947–48 | ||
| 47 | 1948–49 | ||
| 48 | 1949–50 | ||
| 49 | 1950–51 | ||
| 50 | 1951–52 | ||
| 51 | 1952–53 | ||
| 52 | 1953–54 | ||
| 53 | 1954–55 | ||
| 54 | 1955–56 | ||
| 55 | 1956–57 | ||
| 56 | 1957–58 | ||
| 57 | 1958–59 | ||
| 58 | 1959–60 | ||
| 59 | 1960–61 | ||
| 60 | 1961–62 | ||
| 61 | 1962–63 | ||
| 62 | 1963–64 | ||
| 63 | 1964–65 | ||
| 64 | 1965–66 | ||
| 65 | 1966–67 | ||
| 66 | 1967–68 | ||
| 67 | 1968–69 | ||
| 68 | 1969–70 | ||
| 69 | 1970–71 | ||
| 70 | 1971–72 | ||
| 71 | 1972–73 | ||
| 72 | 1973–74 | ||
| 73 | 1974–75 | ||
| 74 | 1975–76 | Seiko[1] | Blake Garden[1] |
| 75 | 1976–77 | Seiko[2] | HKFC[2] |
| 76 | 1977–78 | ||
| 77 | 1978–79 | ||
| 78 | 1979–80 | ||
| 79 | 1980–81 | ||
| 80 | 1981–82 | ||
| 81 | 1982–83 | ||
| 82 | 1983–84 | ||
| 83 | 1984–85 | ||
| 84 | 1985–86 | ||
| 85 | 1986–87 | ||
| 86 | 1987–88 | ||
| 87 | 1988–89 | ||
| 88 | 1989–90 | ||
| 89 | 1990–91 | ||
| 90 | 1991–92 | ||
| 91 | 1992–93 | ||
| 92 | 1993–94 | ||
| 93 | 1994–95 | ||
| 94 | 1995–96 | ||
| 95 | 1996–97 | ||
| 96 | 1997–98 | ||
| 97 | 1998–99 | ||
| 98 | 1999–2000 | ||
| 99 | 2000–01 | ||
| 100 | 2001–02 | ||
| 101 | 2002–03 | ||
| 102 | 2003–04 | ||
| 103 | 2004–05 | Sun Hei | HKFC |
| 104 | 2005–06 | Kitchee | Tung Po |
| 105 | 2006–07 | South China | Fukien |
| 106 | 2007–08 | Eastern | Shatin |
| 107 | 2008–09 | TSW Pegasus | Shatin |
| 108 | 2009–10 | South China | Not held |
| 109 | 2010–11 | Citizen | Southern District |