During his coaching career, he has inherited an NCAA sanctioned Louisiana Tech team and a Kansas State team that had won just nine games the previous season. While improving the Kansas State Wildcats program, he was unable to reach the postseason and was ultimately let go. He went on to work in the athletic department for Texas State before becoming the head coach at UC Riverside. In his first year at UC Riverside, Wooldridge led the team to their first postseason victory in four years; a 62–54 victory over Cal Poly in the first round of the Big West tournament. In his second year, he tied the record for most wins in a season at UC Riverside since moving to the Division I level. His former assistant at Texas State and Kansas State Mike Miller is the head coach at Eastern Illinois University.
National champion Postseason invitational champion Conference regular season champion Conference regular season and conference tournament champion Division regular season champion Division regular season and conference tournament champion Conference tournament champion