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| Macoupin County Boys Basketball Tournament Championships |
| School | # of Championships | Notes |
| Gillespie Miners | 22 | 4 Consecutive Championships (1953-56) |
| Southwestern Piasa Birds | 17 | |
| Staunton Bulldogs | 15 | |
| Mt. Olive Wildcats | 12 | |
| Carlinville Cavaliers | 9 | |
| Bunker Hill Minutemen | 8 | |
| North Mac Panthers | 6 | |
| Benld Indians | 4 | |
| Chesterfield C-Hawks | 4 | |
| Virden Bulldogs | 4 | |
| Girard Big Red | 3 | |
| Brighton Bulldogs | 1 | |
| Hettick Hawks | 0 | |
| Medora Tigers | 0 | |
| Palmyra Panthers | 0 | |
| Shipman Pirates | 0 | |
| Macoupin County Boys Basketball Tournament History |
| Annual | Year | Champion | Head Coach | Host |
| 109th | 2028 | Team | Coach
| Staunton |
| 108th | 2027 | Team | Coach
| MT. Olive |
| 107th | 2026 | Team | Coach
| North Mac |
| 106th | 2025 | Team | Coach
| Carlinville |
| 105th | 2024 | Southwestern | Jason Darr
| Piasa |
| 104th | 2023 | Southwestern | Jason Darr
| Bunker Hill |
| 103rd | 2022 | Southwestern | Jason Darr
| Gillespie |
| DNP | 2021 | Covid | Covid
| Did Not Play |
| 102nd | 2020 | North Mac | T.J. Wilson
| Staunton |
| 101st | 2019 | North Mac | T.J. Wilson
| MT. Olive |
| 100th | 2018 | North Mac | T.J. Wilson
| North Mac |
| 99th | 2017 | Southwestern | Jason Darr
| Carlinville |
| 98th | 2016 | Gillespie | Casey Sholtis
| Piasa |
| 97th | 2015 | Southwestern | Jason Darr
| Gillespie |
| 96th | 2014 | North Mac | T.J. Wilson | Bunker Hill |
| 95th | 2013 | North Mac | T.J. Wilson | Staunton |
| 94th | 2012 | Staunton | Steve Moore | Mt. Olive |
| 93rd | 2011 | North Mac | T.J. Wilson | North Mac |
| 92nd | 2010 | Girard | T.J. Wilson | Northwestern |
| 91st | 2009 | Staunton | Steve Moore | Carlinville |
| 90th | 2008 | Girard | T.J. Wilson | Piasa |
| 89th | 2007 | Southwestern | Larry Lowis | Bunker Hill |
| 88th | 2006 | Southwestern | Larry Lowis | Gillespie |
| 87th | 2005 | Carlinville | Skip Brooks | Staunton |
| 86th | 2004 | Mt. Olive | Doug Zehr | Mt. Olive |
| 85th | 2003 | Gillespie | Terry Allan | Virden |
| 84th | 2002 | Gillespie | Terry Allan | Carlinville |
| 83rd | 2001 | Staunton | Kevin Gockel | Carlinville |
| 82nd | 2000 | Southwestern | Scott Laird | Carlinville |
| 81st | 1999 | Bunker Hill | Jim Hlafka | Carlinville |
| 80th | 1998 | Bunker Hill | Jim Hlafka | Carlinville |
| 79th | 1997 | Carlinville | Quinn Steiner | Carlinville |
| 78th | 1996 | Bunker Hill | Jim Hlafka | Carlinville |
| 77th | 1995 | Gillespie | Quinn Steiner | Carlinville |
| 76th | 1994 | Southwestern | Randy Jackson | Virden |
| 75th | 1993 | Virden | Jerry O'Brien | Girard |
| 74th | 1992 | Staunton | Randy Legendre | Northwestern |
| 73rd | 1991 | Staunton | Mike Stivers | Carlinville |
| 72nd | 1990 | Southwestern | Darrell Burd | Piasa |
| 71st | 1989 | Southwestern | Darrell Burd | Bunker Hill |
| 70th | 1988 | Southwestern | Darrell Burd | Gillespie |
| 69th | 1987 | Staunton | Mike Stivers | Staunton |
| 68th | 1986 | Staunton | Mike Stivers | Virden |
| 67th | 1985 | Staunton | Mike Stivers | Girard |
| 66th | 1984 | Bunker Hill | Jim Hlafka | Northwestern |
| 65th | 1983 | Bunker Hill | Jim Hlafka | Carlinville |
| 64th | 1982 | Staunton | Mike Stivers | Piasa |
| 63rd | 1981 | Bunker Hill | Jim Hlafka | Bunker Hill |
| 62nd | 1980 | Staunton | Mike Stivers | Gillespie |
| 61st | 1979 | Virden | Mike Kaczmarz | Staunton |
| 60th | 1978 | Southwestern | Darrell Burd | Northwestern |
| 59th | 1977 | Virden | Mike Kaczmarz | Carlinville |
| 58th | 1976 | Southwestern | Darrell Burd | Piasa |
| 57th | 1975 | Southwestern | Darrell Burd | Bunker Hill |
| 56th | 1974 | Southwestern | Darrell Burd | Gillespie |
| 55th | 1973 | Girard | Ned Bond | Staunton |
| 54th | 1972 | Gillespie | Jerry Grandone | Carlinville |
| 53rd | 1971 | Southwestern | Dick Well | Bunker Hill |
| 52nd | 1970 | Bunker Hill | Jim Hlafka | Carlinville |
| 51st | 1969 | Gillespie | Bill Parmentier | Gillespie |
| 50th | 1968 | Carlinville | Jim Bottrell | Carlinville |
| 49th | 1967 | Carlinville | Jim Bottrell | Carlinville |
| 48th | 1966 | Bunker Hill | Jim Hlafka | Girard |
| 47th | 1965 | Gillespie | Bill Parmentier | Piasa |
| 46th | 1964 | Gillespie | Bill Parmentier | Piasa |
| 45th | 1963 | Carlinville | Lou Stivers | ? |
| 44th | 1962 | Carlinville | Lou Stivers | Carlinville |
| 43rd | 1961 | Carlinville | Lou Stivers | Gillespie |
| 42nd | 1960 | Gillespie | George Williams | ? |
| 41st | 1959 | Carlinville | Lou Stivers | Carlinville |
| 40th | 1958 | Staunton | Enno Leitz | Carlinville |
| 39th | 1957 | Carlinville | Lou Stivers | Staunton |
| 38th | 1956 | Gillespie | George Berggren | Carlinville |
| 37th | 1955 | Gillespie | Adolph Tenikat | Gillespie |
| 36th | 1954 | Gillespie | Adolph Tenikat | Gillespie |
| 35th | 1953 | Gillespie | Adolph Tenikat | Gillespie |
| 34th | 1952 | Staunton | Joe Jurkanan | Gillespie |
| 33rd | 1951 | Gillespie | Bob Lyons | Gillespie |
| 32nd | 1950 | Benld | Adolph Tenikat | Carlinville |
| 31st | 1949 | Mt. Olive | Harold Voyles | ? |
| 30th | 1948 | Mt. Olive | Harold Voyles | ? |
| 29th | 1947 | Mt. Olive | Harold Voyles | ? |
| 28th | 1946 | Staunton | B.H. Gibbons | ? |
| 27th | 1945 | Gillespie | Emery Martin | ? |
| 26th | 1944 | Gillespie | Emery Martin | ? |
| 25th | 1943 | Gillespie | Emery Martin | ? |
| 24th | 1942 | Mt. Olive | Harold Jester | ? |
| 23rd | 1941 | Gillespie | Leslie Nicolet | ? |
| 22nd | 1940 | Gillespie | Leslie Nicolet | ? |
| 21st | 1939 | Benld | John Rossetti | ? |
| 20th | 1938 | Mt. Olive | Roy Colin | ? |
| 19th | 1937 | Gillespie | Leslie Nicolet | ? |
| 18th | 1936 | Benld | Glenn Hastings | ? |
| 17th | 1935 | Staunton | Cliff Stiegemeier | ? |
| 16th | 1934 | Gillespie | George Gravel | ? |
| 15th | 1933 | Virden | Sam England | ? |
| 14th | 1932 | Gillespie | George Gravel | ? |
| 13th | 1931 | Chesterfield | Ralph Turner | ? |
| 12th | 1930 | Chesterfield | Ralph Turner | ? |
| 11th | 1929 | Chesterfield | Ralph Turner | ? |
| 10th | 1928 | Staunton | Carroll McBride | ? |
| 9th | 1927 | Mt. Olive | J.L. Moore | ? |
| 8th | 1926 | Mt. Olive | J.L. Moore | ? |
| 7th | 1925 | Mt. Olive | James Culberson | ? |
| 6th | 1924 | Chesterfield | Roy McCullom | ? |
| 5th | 1923 | Mt. Olive | Bosie Potthoff | ? |
| 4th | 1922 | Mt. Olive | Bosie Potthoff | ? |
| 3rd | 1921 | Brighton | V.M. Jacobi | Gillespie |
| 2nd | 1920 | Mt. Olive | Paul Seehausen | Mt. Olive |
| 1st | 1919 | Benld | Wm. E. Rutherford | Carlinville |
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