In November 1991 he again signed for Shamrock Rovers, but this spell was less successful and Doolin left after 1 goal in 21 appearances to join Shelbourne where he won the FAI Cup in 1993.
In August 1996, he had his second spell at Bohemians before moving to Dundalk and then returning to Shelbourne and helping them to the double of the league championship and FAI Cup in 2000.
Since his retirement, Doolin has moved into management and first took the reins at UCD, but left to take over at Drogheda with the Students 11 points adrift at the bottom of the table en route to a first relegation in 15 years.
Having parted ways with Drogheda due to the club's precarious financial situation, Doolin joined Cork City as manager on 13 January 2009 on a two-year, full-time contract.
[2] Despite the team finishing 3rd in the 2009 League of Ireland Premier Division, Doolin resigned in November of that year, following a series of off-field financial problems at the club.