| Year | Player | High School | College |
| 1939 | George Crowe | | None |
| 1940 | Ed Scheibein | | |
| 1941 | John Bass | | None |
| 1942 | Bud Brown | | |
| 1943 | No award | ||
| 1944 | No award | ||
| 1945 | Tom Schwartz | | |
| 1946 | Johnny Wilson | | |
| 1947 | Bill Garrett | Shelbyville | |
| 1948 | Bob Masters | | |
| 1949 | Dee Monroe | | |
| 1950 | Pat Klein | | |
| 1951 | Tom Harrold | | |
| 1952 | Joe Sexson | | Purdue |
| 1953 | Hallie Bryant | | |
| 1954 | Bobby Plump | | |
| 1955 | Wilson (Jake) Eison | Gary Roosevelt | Purdue |
| 1956 | Oscar Robertson | | |
| 1957 | John Coalmon | | Fordham |
| 1958 | Mike McCoy | | |
| 1959 | Jimmy Rayl | | |
| 1960 | Ron Bonham | | |
| 1961 | Dick Van Arsdale Tom Van Arsdale | | |
| 1962 | Larry Humes | | |
| 1963 | Rick Jones | | |
| 1964 | Dennis Brady | | Purdue |
| 1965 | Billy Keller | Indianapolis Washington | Purdue |
| 1966 | Rick Mount | Lebanon | Purdue |
| 1967 | Willie Long | Fort Wayne South Side | New Mexico |
| 1968 | Billy Shepherd | Carmel | Butler |
| 1969 | George McGinnis | Indianapolis Washington | Indiana |
| 1970 | Dave Shepherd | Carmel | Indiana, Mississippi |
| 1971 | Mike Flynn | Jeffersonville | Kentucky |
| 1972 | Phil Cox | Connersville | Butler |
| 1973 | Kent Benson | New Castle | Indiana |
| 1974 | Steve Collier Roy Taylor | Southwestern (Hanover) Anderson | Cincinnati Vincennes, Murray State |
| 1975 | Kyle Macy | Peru | Purdue, Kentucky |
| 1976 | Dave Colescott | Marion | North Carolina |
| 1977 | Ray Tolbert | Anderson Madison Heights | Indiana |
| 1978 | David Magley | South Bend LaSalle | Kansas |
| 1979 | Steve Bouchie | Washington | Indiana |
| 1980 | Jim Master | Harding | Kentucky |
| 1981 | Dan Palombizio | Michigan City Rogers | Purdue, Ball State |
| 1982 | Roger Harden | Valparaiso | Kentucky |
| 1983 | Steve Alford | New Castle | Indiana |
| 1984 | Delray BrooksTroy Lewis | Michigan City Rogers Anderson | Indiana, Providence Purdue |
| 1985 | Jeff Grose | Warsaw | Northwestern |
| 1986 | Mark Jewell | | |
| 1987 | Jay Edwards Lyndon Jones | | |
| 1988 | Woody Austin | | Purdue |
| 1989 | Pat Graham | Floyd Central | Indiana |
| 1990 | Damon Bailey | Bedford North Lawrence | Indiana |
| 1991 | Glenn Robinson | Gary Roosevelt | Purdue |
| 1992 | Charles Macon | Michigan City Elston | Ohio State |
| 1993 | *Maurice (Kojak) Fuller | Anderson | Southern |
| 1994 | Bryce Drew | Valparaiso | Valparaiso |
| 1995 | Damon Frierson | Ben Davis | Miami (Ohio) |
| 1996 | Kevin Ault | Warsaw | Southwest Missouri State |
| 1997 | Luke Recker | DeKalb | Indiana, Iowa |
| 1998 | Tom Coverdale | Noblesville | Indiana |
| 1999 | Jason Gardner | North Central (Indianapolis) | Arizona |
| 2000 | Jared Jeffries | Bloomington North | Indiana |
| 2001 | Chris Thomas | Pike | Notre Dame |
| 2002 | Sean May | Bloomington North | North Carolina |
| 2003 | Justin Cage | Pike | Xavier |
| 2004 |
*Title
vacated by Sherron Wilkerson,
