Derrick graduated from Muscle Shoals High School in 1989 where he was an outstanding point guard for the Trojans basketball team. His high school Coach H. L Noah praised him for not only his athletic ability, but his leadership on the hardwood. Coach Noah said, "Derrick was like having a coach on the floor." He averaged 21.9 points per game and shot 64 percent from the floor while on the way to being named Honorable Mention All-State and McDonald's All-American. Following high school he signed a basketball scholarship to continue his basketball career playing for William and Mary University despite fracturing his foot during his senior season which limited his playing time. Once at William and Marry, Derrick continued the success he had in high school as he was a three year letterman. While being valuable as an offensive threat on the hardwood, it was not his ability to score that his opponents remember about his tenacity on the court, but his ability to shut down the best player on the opposing team consistently. He was selected to the 1991 and 1992 Colonial Athletic Association All-Conference Defensive Teams.