The Buckeyes didn't retain him for long before the young star transferred to the Kentucky Wildcats. In the 1994-95 season, he didn’t receive any chance to play. At the same time he was transferred from Ohio State to Kentucky.  As a junior in 1996 Anderson helped the Wildcats win the NCAA National Title and also earned All-NCAA Tournament Honors in 1996-1997. As a senior at Kentucky Derek missed all his games from Jan. 18 through the Final Four, he earned All-SEC Second Team honors and was ranked second on his team with an average of 17.7 points a game, shooting .811 free throws, 3.5 assists, and 1.9 steals. In his four year career, from Ohio State to Kentucky, Anderson finished with 1,228 points, 379rebounds, and 321 assists.

Derek Anderson has reached an unbelievable level of making a three pointer or a precious free throw to win the game just like many of the other NBA athletes. Anderson initiated his NBA career after playing college basketball at Kentucky. In 1997 he entered the NBA Draft, being the 13th overall pick by the Ceveland Cavailers. He was a regular starter for the Cavs and availed every opportunity to open the game. He was named Shick All-Rookie Second team after demonstrating his talents in the NBA. Gradually his averages increased with every passing game and defensive became fantastic but that couldn’t even keep him with Cavailers. Cavailers traded Anderson to the L.A Clippers which was a shock for him but he managed to make some agreements. One of the agreements was that Clippers will trade Derek to the Portland TrailBlazers which somehow didn’t worked out so he choose to take a 1 year contract with Tim There not only he got his shot at his first chance at the playoffs but also he was an NBA Champion.  Without Derek heating it up from the top of the three point line Tim Duncan and David Robinson wouldn't be able to body the opponents down low. Derek was credited with being at the top of his game, being in the best shape of his whole career. The next season he lead his team in steals and ranked second in scoring with 17.8 points per game. The most impressive was his career high 40.6% from three point range connecting on 342 of 402 attempts. In the NBA finals Derek lose four games to zero to the L.A Lakers to an injury. The San Antoino Spurs weren't able to re-sign Derek Anderson to a long term contract so he signed a long term contract with the Portland TrailBlazers.