Darren played his schoolboy football for Kilmore Boys, Grange Woodbine and Belvedere. It was at Belvedere that he was spotted by Millwall and went over to London on a trial. He impressed but while Millwall dithered over a contract offer, Huddersfield Town swooped to bring him to Yorkshire. He made good progress in the reserves but things turned sour for him at the McAlpine Stadium and he was on the verge of a move to Plymouth Argyle when his appendix burst and the move was scuppered. After returning home, Hull City made him an offer of a 6-month contract and Darren returned to England. He began well under Terry Dolan but when Dolan was replaced by Mark Hateley, O'Keeffe soon left.
League of Ireland
His first club in the League of Ireland was Drogheda United under the stewardship of Martin Lawlor. The club was promoted in Darren's first season there and some fine performances in the Premier Division saw the bigger clubs taking notice.
O'Keeffe signed for Bohemians in the summer of 2000 from Drogheda United. The tough tackling midfielder made his debut for the "Gypsies" against Aberdeen in the UEFA Cup. He wrote himself into Bohemian folklore by winning the penalty in the last minute of the game which gave Bohs a famous 2-1 win in Pittodrie. The return leg was not as good for Darren as he received a red card in the first half but Bohs held on to go through on away goals. He scored his first goal for the club in a 1-1 draw with Derry City F.C. in December 2000 but after a training ground bust-up, he was sold to St Patricks Athletic before the end of the 2000/01 season.
Brother of the legendary dean "bambino" Stewart Bolger
- Bohemian FC match programme, Vol. 52, no. 18
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