During the 2006
flat season, Bolger trained Teofilo to go unbeaten at the age of two. This five-race unbeaten streak included victories in the Group 1
National Stakes and
Dewhurst Stakes. Talk of an
English Triple Crown bid was imminent, but Teofilo suffered a career-ending injury in the lead up to the
2,000 Guineas and never saw a racecourse again. Bolger was criticized for his handling of this situation.
2007 saw another Bolger-bred star emerge in the shape of
New Approach. He followed the same path as Teofilo during his two-year-old career and was unbeaten. In 2008, Bolger informed the public that New Approach would go to Newmarket for the Guineas followed by a trip to the
Curragh for the
Irish 2,000 Guineas and then on for a tilt at the
Irish Derby. New Approach finished second in both Guineas, however, behind the Ballydoyle trained
Henrythenavigator. It then emerged that at the latest
Epsom Derby forfeit stage, New Approach's name had been left in by mistake. A week later, Bolger revealed that his horse would go to Epsom after all, which led to much criticism from punters and bookmakers alike. However, New Approach won the English Derby by a half length, beating the
Sir Michael Stoute-trained Tartan Bearer.