From 1998 to 2002, the IceDogs enjoyed little success, finishing last in the OHL's Central Division every year. During this building phase, the team had six head coaches within the span of 4 years, including the owner, Don Cherry. Mississauga drafted first overall each year, leading to two rookies of the year, including one of the highest touted NHL prospects in Jason Spezza. In the 2002–03 season, the IceDogs finished fourth in the Central Division and made the playoffs for the first time in franchise history, but lost in the first round in five games against the Ottawa 67's.