Doolan began his career as a trainee with the club he supports,
Everton in 1992. He was released by Everton and joined
Football League Third Division side
Mansfield Town on a free transfer in September 1994. Doolan joined Football Conference side
Doncaster Rovers for a nominal fee in March 2003. He made eight appearances in the remainder of the
2002–03 season as Doncaster went on to win the Conference play-off final and promotion to the Football League Third Division in May 2003. He became a regular in the first team in the
2003–04 season, making 41 league and cup appearances, scoring three goals, He signed a new contract in December 2003, keeping him at Doncaster until 2005. He made 41 appearances, scoring three goals, in all competitions in the 2004–05 season as Doncaster finished in mid-table in
Football League One. He made 24 appearances for Blackpool in all competitions in the
2005–06 season, He made 18 appearances in the remainder of the 2005–06 season as Rochdale finished in mid-table. He made 44 league and cup appearances in the 2006–07 season. In the
2007–08 season he made 28 appearances as Rochdale made the play-offs, including coming on an extra-time substitute in their 2–1 play-off semi-final victory over
Darlington. ==Coaching career==