As a senior, Gottlieb again led the NCAA in assists, with 293, and finished second in the nation in assists per game with 8.6. He was 7th in the Big 12 in both steals, with 53, and games, with 34. Gottlieb's senior season ended with a third consecutive trip to the NCAA tournament, and the team made it all the way to the Elite Eight. In addition to being named All-Big 12 Honorable Mention his senior year at Oklahoma State, Gottlieb was named the 1999 Big 12 Scholar Athlete Community Service Athlete of the Year.