He attended Central City High School where he played basketball for head coach George Taylor. Central City went 116-20 during Hickman's four years in high school. They won four region championships and went to four State Tournaments where he made the All-State Tournament team in 1929 and 1931. He was also an all-state basketball player two seasons in 1930-31.
College
He lettered three seasons at guard at Western Kentucky for head coach Ed Diddle. WKU went 83-25 during Hickman's four years in college. They won four KIAC Tournament Championships and one SIAA Tournament Championship. He made the Kentucky All-State team in 1933 and 1934, the ALL-KIAC Tournament team in 1935, and the ALL-SIAA Tournament team in 1934 and 1935. He graduated from WKU in 1935 with a bachelor's degree in physical education. He completed his master's degree in physical education at the University of Kentucky College of Education in 1944.
Coaching career
High school
Hickman coached Hodgenville High School and Valley High School to a combined 216-49 record. He led Valley to the Kentucky Sweet 16 twice.
University of Louisville
Hickman was hired as head coach and athletic director at Louisville in 1944> He guided his first team to a 16-4 record. Prior to his arrival the program only had 11 winning seasons in 33 years of play. The Cardinals never had a losing season in Hickman's 23 seasons as head coach. He led Louisville to their first championship on a national level by winning the NAIB Championship in 1948. In 1956, his team headed by All AmericanCharlie Tyra won the NIT Championship. In 1956 his team was placed on two years probation, to include bans on postseason play, by the NCAA due to recruiting violations. In 1959 he led the Cardinals to their first NCAA Tournament Final Four. From 1954 to 1967, Hickman doubled as head coach and athletic director, a position he would hold full-time until his retirement in 1973. One of Hickman's last acts as athletic director was to hire UCLA assistant coach Denny Crum, who would lead the program to two NCAA titles and six final fours en route to the College Basketball hall of fame. In 24 years, Hickman compiled a record of 443-183. Hickman graduated 82 percent of his players, and was the first basketball coach in Kentucky to break the color barrier in 1962, by recruiting Eddie Whitehead, and Wade Houston.