During his second year in Stillwater, Gottlieb led the NCAA in assists, with 299, and also led the nation in assists per game, with 8.8, only the second Cowboy to lead the nation in a statistical category. He also started setting Oklahoma State assist records, breaking the school career mark with 500 (after only two seasons) and broke the school record of 22 career double-figure assist games. In a game against Florida Atlantic, Gottlieb set a school record and tied the Big 12 mark with 18 assists, and in the Big 12 tournament, he set the record for assists in a game (14) as well as in tournament play (38). He led the Big 12 in games, with 34. The 1998–99 season culminated with another trip to the NCAA tournament.