Kirkland started his career at Coventry City, where he was regarded as one of the country's most promising young goalkeepers. He was later signed by Premier League club Liverpool for £6 million in August 2001. However, his time at the club was blighted by recurring injuries, which almost caused him to retire from football altogether. He would later sign for Wigan Athletic in July 2006, after a successful loan period, and he had further loan spells at both Leicester City and Doncaster Rovers before being signed by Sheffield Wednesday in May 2012. He joined Preston North End in August 2015, and had a brief spell with Bury before retiring in August 2016.