Dolan signed YTS forms with Arsenal when he turned sixteen and made numerous appearances for both the youth and reserve team.
After Rovers maiden season in the RDS Arena (3 goals in 23 total appearances) he joined St Patrick's Athletic on a full-time deal in 1991.
Dolan worked closely with manager Brian Kerr and new chairman Tim O'Flaherty (a respected local businessman), and in December 1993 St Pats returned to Richmond Park.
Chairman O'Flaherty surprised most with his appointment of Dolan for team manager with most commentators believing that Kerr's assistant Liam Buckley would get the job.
His use of terms like 'Dublin Saints' and 'Pats-Francis' in both his programme notes and his column for national newspaper the Irish Daily Star angered many Pats fans and in a stormy meeting held by the club to announce their plans, many sought his resignation.
The following season saw the Saints improve dramatically on the pitch and they were leading the league when the FAI announced they were deducting 9 points from St Pats total as they played an ineligible player, Paul Marney, for 3 games.
The FAI overturned this decision and re-instated the nine points, much to the annoyance of closest rivals, Shelbourne's chief executive Oliver Byrne.
After receiving an anonymous tip off, the league investigated the registration of every St Pats player and found that one, Charles Livingstone Mbabazi, wasn't correct.
St Pats, again, angrily denied the charges and a leaked report (to the Evening Herald) commissioned by new league CEO Roy Dooney apparently exposed several minor irregularities in player registrations on several teams but was never released.
St Pats started the season as they ended the previous one and for the first time progressed in Europe beating HNK Rijeka in the Intertoto Cup.
It left St Pats fans divided with the following season seeing many terrace debates between Pro and Anti Dolan camps.
Cork had finished in fourth place in 2002/2003 but with the exciting partnership of John O'Flynn and George O'Callaghan, many pundits expected their challenge to be stronger.
The following season, Dolan invested heavily in players and it seemed to pay off as Cork beat Malmö FF and NEC Nijmegen in the Intertoto Cup before falling to Nantes.
Dolan had finished building a strong team at Cork, following the good work first laid out by Dave Barry and then Liam Murphy, and the club went on to win the league title in 2005 under new manager Damien Richardson, with the notable addition of Roy O'Donovan.
However, Dolan's appointment inspired Waterford United to a remarkable turnaround, and eventually the team secured their status in the league comfortably with two games to spare.
[6] Throughout his St Pats and Cork City days Dolan wrote a weekly column in the tabloid newspaper Irish Daily Star.
On 7 December 2009, in his weekly Star column, Dolan was fiercely critical of the Irish international team's pursuit of players born outside Ireland.
Through his weekly column in the Irish Daily Star and regular appearances on Setanta Sports, Dolan was fiercely critical of the FAI's recruitment process to find a new senior International team manager.