It didn’t take long for Harry’s first Listed winner to arrive. In just his second full season training the three-year-old CLASSIC REMARK, owned by Hesmonds Stud, won the Hoppings Stakes at Newcastle on 26th June 2008 at odds of 40-1 on soft ground to the great delight of her trainer and owners.
In 2007, Harry’s first full season as a trainer, FESTOSO gave him a taste of competing at the highest level when running in Group 1 and Group 2 races. After winning a maiden race at Newmarket the two-year-old returned to the track for her third start where she finished second in the Group 2 Cherry Hinton, beaten just a neck by Youresothrilling.
She finished the season third to subsequent 1,000 Guineas winner and European Champion two-year-old Natagora in the Group 1 Cheveley Park at Newmarket. Despite being plagued with injuries she won Black Type races as a three- and four-year-old and sold for £500,000 at Tattersalls sales.
On 2nd November 2006 Harry sent out his first runner and first winner when SITULA made all under Dane O'Neill at Wolverhampton to give Harry a 100% record.