Dickey was a three time HBCU All-American at Tennessee State University. He completed his collegiate career with 6,523 passing yards and 67 touchdowns. Dickey was considered a gifted athlete with his strongest positions being quarterback and punter. He was also able to throw precision passes with both his left and right arm. With Dickey under center, the 1966 TSU team earned their first undefeated, untied season and their first National Black College Football Championship. In 1968, Dickey was drafted in the first round by the Oakland Raiders.