Dailey was a three-year starter for the Northwestern Wildcats. He recorded 26 tackles for a loss and 12 sacks his senior year in 1997. He was named the Wildcats Defensive player of the year and earned first team All-Big Ten honors as a senior. Dailey was also invited to East–West Shrine Game, Blue–Gray Football Classic and Hula Bowl in 1997. He accumulated 45 tackles and team high eight sacks his junior season. He returned a fumble 45 yards for a touchdown his sophomore year.