Dolan began his career with Motherwell in the late 1980s and was at Fir Park for ten years before transferring to Dundee United at the start of the 1997–98 season. Within four months, Dolan reached the League Cup final with United, although he was as unused substitute despite featuring in each of the previous rounds. After two years at Tannadice, Dolan moved to Dunfermline, where he stayed for one season. A year at Livingston followed, which included a loan deal with Forfar Athletic and he spent his final playing season with Partick Thistle, retiring in 2002 after over 300 league games.