Derek James was a two-sport standout in men's basketball and men's golf from 1999-2003 for the Highlanders. On the links he had a career average of 78 strokes and was Second Team All-SLIAC in 2002. As a senior he won four tournaments and had a 74.5 average. James also won the 2003 SLIAC Championship and was named SLIAC Player of the Year and First Team All-SLIAC. On the hardwood James was a three-time All-SLIAC honoree, earning First Team in 2001-02 and 2002-03 and Second Team in 2000-01. In addition, he was a member of the Highlanders' squad in 2000-01 that qualified for the NCAA Division III Tournament, the only team in program history to do so. James was also named team MVP in his senior year (2002-03). In the record books, James is MacMurray's all-time leader in three-point field goals made with 228. He also ranks in the career top 10 in steals (6th), assists (10th) and scoring (7th). He finished his career with 1,280 points and was inducted into the MacMurray Athletic Hall of Fame in 2009.