Dolan began his career with Motherwell in the late 1980s and was at Fir Park for ten years before transferring to Dundee United during the 1996–97 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.
He was a mainstay in the heart of the Motherwell midfield in the early to mid-nineties and formed part of a famous trio containing Paul Lambert and Billy Davies in 'Well's fantastic team of 1994–1996.
In one game on 7 December 1996, having started in his usual midfield role, he even played in goal for the last 30 minutes against Celtic when Motherwell goalkeeper Scott Howie was taken off injured.
Jamie played for the Motherwell Masters team and was a pivotal member of the squad that took the 2007 title, scoring the last goal in the final against Celtic.