McCann started his career with Wolves Boys Club in Glasgow[2] and then became an apprentice with Scottish League First Division Airdrieonians in 1997.

He spent 3 successful seasons with Airdrie, playing 97 times and scoring 9 goals while gaining a reputation as an exciting young talent.

His form attracted the attention of Premier League side Heart of Midlothian, who were seeking a replacement for the recently sold Gary Naysmith, and he moved to the Edinburgh club in February 2001.

[3] McCann left Hearts in April 2004 in search of more regular first team football, initially signing a short-term deal with Clyde before agreeing to join Steve Evans' growing Scottish contingent at Boston United in the summer.

McCann played 88 games in two seasons for the Pilgrims, scoring 1 goal against Cambridge United,[4] before joining Notts County when his contract at York Street expired in the summer of 2006.