Seir Kieran went through a drought of success for the majority of the next eight years. After failing to make it two county titles in-a-row in 1989, Dooley's club lost championship deciders to Birr in 1991 and again in 1994. In 1995 Seir Kieran qualified for the club championship decider again after defeating reigning county, provincial and All-Ireland club champions Birr in the semi-final. St Rynagh's provided stiff opposition in the county final, however, Seir Kieran looked to be heading towards their second championship ever. An equalising goal by St. Rynagh's in the second minute of injury time secured a draw and a replay. Seir Kieran won the replay a week later and Dooley secured his second county championship title and was captain of the side. Both Seir Kieran and St. Rynagh's met again in the championship decider of 1996 and, once again, the game was a close affair. Dooley's side were two points in arrears with two minutes to go, however, Seir Kieran battled back to win by 0-13 to 1-8. It was a third county title for Dooley. In 1997 Seir Kieran had the chance to make it three title in-a-row. All was going to plan as Dooley's side qualified for the championship decider with Birr. The game developed into a tight affair, however, Birr pulled away in the last ten minutes to secure a 0-14 to 2-4 victory. A fourth championship decider in succession beckoned for Dooley's side in 1998 with old rivals St. Rynagh's providing the opposition. This game ended in a draw, and the replay saw Dooley pick up a fourth county championship winners' medal following a 1-11 to 0-8 victory. After failing to retain the title in 1999, Seir Kieran were back in the millennium championship decider. Birr easily won the game by 3-21 to 1-9. By 2006 Dooley had retired from the Seir Kieran senior hurling team, however, he lined out for club's junior team in the championship decider that year. St. Rynagh's provided the opposition, however, Seir Kieran claimed the title. Dooley enjoyed a successful colleges career, winning five Leinster colleges medals, and played in two all-Ireland senior colleges finals with Presentation Brothers College Birr. He joined the Offaly senior hurling panel in April 1982.