| Year | Player | High School | College | NBA Draft |
| 1954 | Vernon Hatton | Lafayette | Kentucky | 1958 NBA draft: 2nd round, 10th overall by the Cincinnati Royals |
| 1955 | Kenny Kuhn | Male | | |
| 1956 | Kelly Coleman | Wayland | Kentucky Wesleyan | 1960 NBA draft: 2nd round, 11th overall by the New York Knicks |
| 1957 | Billy Ray Lickert | Lafayette | Kentucky | 1961 NBA draft: 5th round, 45th overall by the L.A. Lakers |
| 1958 | Ralph Richardson | Russell County | Eastern Kentucky | |
| 1958 | Harry Todd | Earlington | Western Kentucky | |
| 1959 | Pat Doyle | North Marshall | Kentucky | |
| 1960 | Jeff Mullins | Lafayette | Duke | 1964 NBA draft: 1st round, 5th overall by the St. Louis Hawks |
| 1961 | Randy Embry | Owensboro | Kentucky | |
| 1962 | Mike Silliman | St. Xavier | Army | 1966 NBA draft: 8th round, 69th overall by the New York Knicks |
| 1963 | Mike R. Redd | Seneca | Kentucky Wesleyan | |
| 1964 | Wes Unseld | Seneca | Louisville | 1968 NBA draft: 1st round, 2nd overall by the Baltimore Bullets |
| 1965 | Butch Beard | Breckinridge County | Louisville | 1969 NBA draft: 1st round, 10th overall by the Atlanta Hawks |
| 1966 | Mike Casey | Shelby County | Kentucky | |
| 1967 | Jim McDaniels | Allen County | Western Kentucky | 1971 NBA draft: 2nd round, 23rd overall by the Seattle SuperSonics |
| 1968 | Terry Davis | Shelby County | Western Kentucky | |
| 1969 | Ron King | Central | Florida State | |
| 1970 | Robert Brooks | Madison | Eastern Kentucky | |
| 1971 | Jimmy Dan Conner | Anderson County | Kentucky | 1975 NBA draft: 2nd round, 36th overall by the Phoenix Suns |
| 1972 | Jerry Thruston | Owensboro | Mercer | |
| 1973 | Wesley Cox | Male | Louisville | 1977 NBA draft: 1st round, 18th overall by the Golden State Warriors |
| 1974 | Jack Givens | Bryan Station | Kentucky | 1978 NBA draft: 1st round, 16th overall by the Atlanta Hawks |
| 1975 | Dom Fucci | Tates Creek | Auburn | |
| 1976 | Darrell Griffith | Male | Louisville | 1980 NBA draft: 1st round, 2nd overall by the Utah Jazz |
| 1977 | Jeff Lamp | Ballard | Virginia | 1981 NBA draft: 1st round, 15th overall by the Portland Trail Blazers |
| 1978 | Doug Schloemer | Holmes | Cincinnati | |
| 1979 | Dirk Minniefield | Lafayette | Kentucky | 1983 NBA draft: 2nd round, 33rd overall by the Dallas Mavericks |
| 1980 | Ervin Stepp | Phelps | Eastern Kentucky Alice Lloyd College | |
| 1981 | Phil Cox | Cawood | Vanderbilt | |
| 1982 | Todd May | Virgie | Kentucky Pikeville | 1987 NBA draft: 4th round, 73rd overall by the San Antonio Spurs |
| 1983 | Winston Bennett | Male | Kentucky | 1988 NBA draft: 3rd round, 64th overall by the Cleveland Cavaliers |
| 1984 | Steve Miller | Henry Clay | Western Kentucky | |
| 1985 | Tony Kimbro | Seneca | Louisville | |
| 1986 | Rex Chapman | Apollo | Kentucky | 1988 NBA draft: 1st round, 8th overall by the Charlotte Hornets |
| 1987 | John Pelphrey | Paintsville | Kentucky | |
| 1988 | Richie Farmer | Clay County | Kentucky | |
| 1989 | Allan Houston | Ballard | Tennessee | 1993 NBA draft: 1st round, 11th overall by the Detroit Pistons |
| 1990 | Dwayne Morton | Louisville Central | Louisville | 1994 NBA draft: 2nd round, 45th overall by the Golden State Warriors |
| 1991 | Jermaine Brown | Fairdale | Georgetown (KY) | |
| 1992 | Tick Rogers | Hart County | Louisville | |
| 1993 | Jason Osborne | Male | Louisville | |
| 1994 | Elton Scott | Marion County | West Virginia | |
| 1995 | Charles Thomas | Harlan | Eastern Kentucky | |
| 1996 | Daymeon Fishback | Greenwood | Auburn | |
| 1997 | Brandon Davenport | Owensboro | Lindsey Wilson College | |
| 1998 | J. R. VanHoose | Paintsville | Marshall | |
| 1999 | Rick Jones | Scott County | Vanderbilt Murray State | |
| 2000 | Scott Hundley | Scott County | Vanderbilt | |
| 2001 | Josh Carrier | Bowling Green | Kentucky | |
| 2002 | Brandon Stockton | Glasgow | Kentucky | |
| 2003 | Ross Neltner | Highlands | LSU Vanderbilt | |
| 2004 | Chris Lofton | Mason County | Tennessee | |
| 2005 | Domonic Tilford | Jeffersontown | South Alabama | |
| 2006 | Walt Allen | South Laurel | Presbyterian | |
| 2007 | Steffphon Pettigrew | Elizabethtown | Western Kentucky | |
| 2008 | Darius Miller | Mason County | Kentucky | 2012 NBA draft: 2nd round, 46th overall by the New Orleans Hornets |
| 2009 | Jon Hood | Madisonville North Hopkins | Kentucky | |
| 2010 | Elisha Justice | Shelby Valley | Louisville Pikeville | |
| 2011 | Anthony Hickey | Christian County | LSU Oklahoma State | |
| 2012 | Nathan Dieudonne | Trinity | Boston University | |
| 2013 | Dominique Hawkins | Madison Central | Kentucky | |
| 2014 | Quentin Snider | Ballard | Louisville | |
| 2015 | Camron Justice | Knott County Central | Vanderbilt IUPUI Western Kentucky | |
| 2016 | Carson Williams | Owen County | Northern Kentucky Western Kentucky | |
| 2017 | Taveion Hollingsworth | Dunbar | Western Kentucky | |
| 2018 | Trevon Faulkner | Mercer County | Northern Kentucky | |
| 2019 | Dontaie Allen | Pendleton County | Kentucky Western KY | |
| 2020 | Dayvion McKnight | Martha Layne Collins | Western Kentucky | |
| 2021 | Ben Johnson | Lexington Catholic | Bellarmine | - |
| 2022 | Turner Buttry | Bowling Green | Eastern Kentucky | |
| 2023 | Reed Sheppard | North Laurel | Kentucky | 2024 NBA draft: 1st round, 3rd overall by the Houston Rockets |
| 2024 | Travis Perry | Lyon County | Kentucky | - |
| 2025 | Malachi Moreno | Great Crossing | Kentucky | - |