After going to Doss High School he went to play for Ohio State. The Buckeyes didn't hold on to him for long before the young star transfered to the Kentucky Wildcats. He was forced to sit out the 1994-95 season while he transfered from Ohio State to Kentucky. He made the switch in 95 and stayed with the fighting Wildcats. While he was with the Wildcats, half his team famed while he laid low helping the "Thunder and Lightning," Duo, rule the college basketball world.
As a junior in 1996 Anderson helped the Wildcats win the NCAA National Title, while also earning All-NCAA Tournament Honors in 1996-1997. Also in 1997 the now well know star made on spot on the 1997 All-American team. As a senior at Kentucky Derek missed all his games from Jan. 18 through the Final Four, he earned All-SEC Second Team honors. At Kentucky he came in second on his team scoring an average of 17.7 points a game, shooting .811 free throws, 3.5 assists, and 1.9 steals. In his four year career going from Ohio State to Kentucky, Anderson finished with 1,228 points, 379 rebounds, and 321 assists.