Dolan played as a striker, beginning his professional career with West Ham United.

He made his debut on 9 May 1987 in a 2–0 home win against Manchester City coming on as a substitute for Mark Ward.

In 5–0 home defeat of Sunderland, he scored twice with his goal celebrations inspiring cartoons drawn by fanzine cartoonist, Phill Jupitus.

[2][3] He continued to play regularly until the end of November 1989 when he signed for Birmingham City[1] He made 21 appearances in all competitions for West Ham scoring four goals.

[5] His first season in charge was fairly successful, steadying the ship after a difficult year, and almost qualifying for the playoffs, but he left the club in September 2004 to join Reading as academy manager.