O'Connor and Custom Made made their debut at Rolex Kentucky Three Day in the CCI*** division in 1995. The pair won the dressage phase by almost 12 penalty points, but the horse was a run-away on cross-country and had 11. 5 penalties in the show jumping. Although O'Connor and Custom Made were able to win their first three-day by a slim margin of 0. 1 penalties, it was clear that the horse needed additional training before he could be truly successful.