2020–Simeon 81, Morgan Park 76
2019–Curie 65, Morgan Park 60
2018–Simeon 69, Orr 59
2017–Simeon 68, Morgan Park 64
2016–Simeon 54, Kenwood 49
2015–Bogan 47, Simeon, 42
2014–Curie 69, Young 66 4 OT, (later forfeited)
2013–Young 60, Morgan Park 56, OT
2012–Simeon 53, Curie 49
2011–Brooks 67, Young 54
2010–Morgan Park 61, Marshall 60
2009–North Lawndale 54, Hyde Park 51, OT
2008–Marshall 55, Farragut 51
2007–Simeon 89, Washington 57
2006–Simeon 55, Washington 40
2005–Westinghouse 67, Simeon 52
2004–Westinghouse 60, Simeon 48
2003–Crane 80, Julian 68
2002–Westinghouse 62, Farragut 58
2001–Morgan Park 67, Crane 60
2000–Westinghouse 82, Young 60
1999–King 59, Westinghouse 39
1998–Young 67, King 46
1997–Young 72, Manley 50
1996–Westinghouse 55, Farragut 46
1995–Farragut 71, Carver 62
1994–Westinghouse 59, King 58
1993–King 77, Westinghouse 52
1992–Westinghouse 76, King 68
1991–Marshall 58, Westinghouse 38
1990–King 83, Westinghouse 48
1989–King 67, Simeon 57
1988–Simeon 66, King 59
1987–King 93, Crane 66
1986–King 49, Simeon 46
1985–Simeon 65, Carver 54
1984–Simeon 44, Robeson 42
1983–Marshall 67, Collins 62, 2 OT
1982–Marshall 58, Crane 48
1981–Westinghouse 79, Marshall 66
1980–Manley 67, Collins 55
1979–Manley 88, Westinghouse 83, 2 OT
1978–Westinghouse 71, Manley 68
1977–Phillips 77, Westinghouse 65
1976–Morgan Park 75, Vocational 60
1975–Phillips 65, Morgan Park 60
1974–Morgan Park 84, Phillips 73
1973–Hirsch 55, Parker 53
1972–Crane 75, Marshall 63
1971–Harlan 44, Tilden 38
1970–Harlan 72, DuSable 63
1969–Hirsch 72, Bowen 66
1968–Crane 75, Marshall 65
1967–Harlan 60, DuSable 56
1966–Marshall 81, Dunbar 68
1965–Marshall 69, DuSable 55
1964–Crane 63, Dunbar 58
1963–Carver 57, Harlan 51
1962–Carver 47, Marshall 39
1961–Marshall 64, DuSable 61
1960–Marshall 79, Crane 38
1959–Marshall 61, Crane 58
1958–Marshall 68, Dunbar 59
1957–Crane 66, Marshall 61
1956–Dunbar 79, Hyde Park 68
1955–Marshall 67, Crane 57
1954–DuSable 82, Lake View 65
1953–DuSable 82, Wells 74
1952–Roosevelt 63, Tilden 62
1951–Parker 64, Von Steuben 58
1950–Tilden 45, Vocational 35
1949–Tilden 54, Marshall 49
1948–Marshall 57, Von Steuben 32
1947–South Shore 58, Lane 38
1946–Tilden 59, Amundsen 51
1945–Senn 32, Von Steuben 20
1944–South Shore 51, Harper 37
1943–Kelvyn Park 28, Lindblom 26, OT
1942–Lindblom 41, Kelly 25
1941–Manley 38, Marshall 34
1940–Crane 35, Hirsch 23
1939–Lane 30, Hirsch 25
1938–Von Steuben 27, Hyde Park 24
1937–Wells 23, Farragut 21
1936–Farragut 23, Kelvyn Park 21
1935–Tilden 33, Senn 24
1934–Lane 29, Tilden 16
1933–Lake View 25, Bowen 17
1932–Crane 25, Calumet 21
1931–Crane 30, Phillips 22
1930–Phillips 20, Morgan Park 19
1929–Crane 23, Lindblom 17
1928–Crane 20, Englewood 19
1927–Englewood 20, Lane 17
1926–Lane 31, Englewood 17
1925–Hyde Park 17, Lake View 11
1924–Lane 18, Phillips 4
1923–Tilden 30, Hyde Park 11
1922–Austin 27, Lane 9
1921–Crane 21, Hyde Park 8
1920–Lane 15, Hyde Park 15, tie
1919–Schurz 17, Englewood 12
1918–Englewood 21, McKinley 8
1917–Phillips 22, Lane 11
1916–Hyde Park 24, Marshall 20
1915–Lane 23, Calumet 7
1914–Parker 18, Lane 16
1913–Hyde Park 11, Englewood 9
1912–Hyde Park 19, Lyons 18
1911–Lane 34, Hyde Park 29
1910–Englewood 30, Calumet 18
1909–Lake View 40, Calumet 17
1908–Lake 25, Austin 21
1907–Lake View 24, Austin 21
1906–Oak Park 21, Austin 14
1905–Austin 62, Lake 22
1904–North Division 26, Austin 19
1903–North Division 41, Medill 14
1902–Medill 16, Lake 15
1901–Hyde Park 23, North Division 22, OT