CHAMPIONSHIP MEN'S DIVISION
| Year | Name and City | W/L | Average | |
| 1921 | T. P. Storey | Unk. | Unk. | |
| 1922 | E. M. Merchant | Unk | Unk. | |
| 1923 | J. W. Netherton | Unk | Unk. | |
| 1924 | L. P. Soete | Unk. | Unk. | |
| 1925 | Leonard Miller- Louisville | Unk. | Unk. | |
| 1926 | Ed Beckman- Louisville | 4-1 | Unk. | |
| 1927 | Sam Mattingly- Louisville | 14-2 | 38.0% | |
| 1928 | Ed Beckman- Louisville | 9-0 | 48.9% | |
| 1929 | Lee Akers- Nolin | 14-1 | Unk. | |
| 1930 | Sam Mattingly- Louisville | Unk. | Unk. | |
| 1931 | Lee Akers- Nolin | 8-1 | 46.0% | |
| 1932 | William Nuttall- Louisville | 15-0 | 52.0% | |
| 1933 | Lee-Akers- Nolin | 14-1 | 50.0% | |
| 1933 | George Moore- Dayton | 9-0 | 48.4% | |
| 1934 | Lee Akers- Nolin | 10-3 | Unk. | |
| 1934 | Harry Henn- Cold Springs | Unk. | Unk. | |
| 1935 | Van L. Young- Shelbyville | 9-0 | 58.5% | |
| 1935 | Harry Henn- Cold Springs | Unk. | Unk. | |
| 1936 | Van L. Young- Shelbyville | Unk. | Unk. | |
| 1936 | Harry Henn- Cold Springs | Unk. | Unk. | |
| 1937 | Van L. Young- Shelbyville | Unk. | 65.1% | |
| 1937 | George Moore- Dayton | 12-1 | 56.0% | |
| 1938 | Elmer McCoy- Louisville | Unk. | 67.0% | |
| 1938 | George Moore- Dayton | 14-1 | 61.4% | |
| 1939 | Elmer McCoy- Louisville | 9-0 | 62.0% | |
| 1940 | Elmer McCoy- Louisville | 9-0 | 64.0% | |
| 1941 | Elmer McCoy- Louisville | 9-1 | 59.1% | |
| 1942 | Robert M. Cartwright- Louisville | 5-2 | 48.0% | |
| 1944 | Alvey Keene- Louisville | Unk. | 55.0% | |
| 1945 | Alvey Keene- Louisville | 7-0 | 52.7% | |
| 1946 | Earl Morris- Fern Creek | Unk. | 62.0% | |
| 1947 | Jim Johnson- Ludlow | Unk | Unk | |
| 1948 | Jim Johnson- Ludlow | Unk | Unk | |
| 1949 | Jim Johnson- Ludlow | 5-0 | 82.5% | |
| 1950 | Jim Johnson- Ludlow | 5-0 | 67.8% | |
| 1965 | George Fraley- Ashland | Unk. | Unk. | |
| 1967 | Howard Hamilton- Georgetown | 9-1 | 53.4% | |
| 1968 | Vern Hawkins- Burlington | 10-1 | 52.8% | |
| 1969 | Bill Henn- Bellevue | 15-1 | 65.4% | |
| 1970 | Howard Hamilton- Georgetown | 9-1 | 64.3% | |
| 1971 | Bill Henn- Bellevue | 9-1 | 70.2% | |
| 1972 | Bill Henn- Bellevue | 15-0 | 72.0% | |
| 1973 | Bill Henn- Bellevue | 14-1 | 69.5% | |
| 1974 | Bill Henn- Bellevue | 9-0 | 69.3% | |
| 1975 | Bill Henn- Bellevue | 10-1 | 68.7% | |
| 1976 | Jack Fahey- Lexington | 10-1 | 70.4% | |
| 1977 | Jack Fahey- Lexington | 10-1 | 73.3% | |
| 1978 | Jack Fahey- Lexington | 10-1 | 74.7% | |
| 1979 | Jack Fahey-Lexington | 11-0 | 70.4% | |
| 1980 | Jack Fahey- Lexington | 11-0 | 76.9% | |
| 1981 | Rube Blevins- Preston | 9-2 | 60.6% | |
| 1982 | Rube Blevins- Preston | 7-0 | 67.1% | |
| 1983 | Ed Henry- Lexington | 6-1 | 59.7% | |
| 1984 | Bill Henn- Bellevue | 6-1 | 65.9% | |
| 1985 | Ed Curran- Paris | 6-1 | 58.8% | |
| 1986 | Ron Powell- Henderson | 9-0 | 71.9% | |
| 1987 | Ron Powell- Henderson | 8-1 | 71.7% | |
| 1988 | Ron Powell- Reed | 15-0 | 72.1% | |
| 1989 | Ron Powell- Reed | 11-0 | 77.8% | |
| 1990 | Charlie Meredith- Chalybeate | 9-0 | 73.1% | |
| 1991 | Ron Powell- Reed | 9-0 | 79.7% | |
| 1992 | Charlie Meredith- Chalybeate | 8-1 | 78.8% | |
| 1993 | Don Titcomb- Winchester | 9-1 | 76.0% | |
| 1994 | Don Titcomb- Winchester | 8-1 | 74.0% | |
| 1995 | Charlie Meredith- Chalybeate | 9-0 | 75.7% | |
| 1996 | Charlie Meredith- Chalybeate | 6-1 | 79.2% | |
| 1997 | Charlie Meredith- Chalybeate | 7-0 | 76.5% | |
| 1998 | Charlie Meredith- Chalybeate | 6-2 | 69.2% | |
| 1999 | Greg Nalley- Bardstown | 7-1 | 70.3% | |
| 2000 | Bill Garrett- Finley | 6-1 | 60.3% | |
| 2001 | Tony Hankins- Louisville | 5-1 | 70.9% | |
| 2002 | Tony Hankins- Louisville | 7-0 | 67.4% | |
| 2003 | Tony Hankins- Louisville | 7-0 | 68.8% | |
| 2004 | Walter Mullins- Middlesboro | 8-2 | 63.1% | |
| 2005 | Tony Hankins- Louisville | 9-1 | 62.6% | |
| 2006 | Walter Mullins- Middlesboro | 8-1 | 66.3% | |
| 2007 | Tony Hankins- Louisville | 9-0 | 63.5% | |
| 2008 | Jim Culver- Henderson | 8-1 | 54.2% | |
| 2009 | Tony Hankins- Louisville | 9-0 | 70.8% | |
| 2010 | John Neagle- Smiths Grove | 8-1 | 58.9% | |
| 2011 | Ricky Bell- Lexington | 8-2 | 62.5% | |
| 2012 | Charlie Meredith- Chalybeate | 9-0 | 71.8% | |
| 2013 | Charlie Meredith- Chalybeate | 9-1 | 66.2% | |
| 2014 | Charlie Meredith- Chalybeate | 9-0 | 76.2% | |
| 2015 | Charlie Meredith- Chalybeate | 7-0 | 76.0% | |
| 2016 | Tony Hankins- Louisville | 7-0 | 66.4% | |
| 2017 | Tyler Howard- Richmond | 7-0 | 73.8% | |
| 2018 | Charlie Meredith- Chalybeate | 7-1 | 66.9% | |
| 2019 | Tyler Howard- Richmond | 7-0 | 81.6% | |
| 2020 | Tyler Howard- Richmond | 7-0 | 82.9% | |
| 2021 | Tyler Howard- Richmond | 7-0 | 73.2% | |
| 2022 | Tyler Howard- Richmond | 7-0 | 72.8% | |
| 2023 | Tyler Howard- Richmond | 7-0 | 76.6% | |
| 2024 | Tyler Howard- Richmond | 7-0 | 77.3% |
For additional information contact Robert Taylor
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