McCann started his career with Dundee before moving on to Heart of Midlothian in 1996. He helped the Tynecastle side win the Scottish Cup in 1998, their first major trophy in 36 years. McCann moved to Rangers later that year for £1.9 million, becoming the club's first major Scottish Catholic signing since Mo Johnston. He scored two goals in a 3–0 win for Rangers against their arch-rivals Celtic on 2 May 1999, which clinched the 1998–99 Scottish Premier League title. McCann left Rangers in 2003, as the club were forced to sell him due to financial problems. Speaking in February 2019, McCann said that he had been subject to sectarian abuse from Celtic fans that stemmed from his decision to sign for Rangers.