 In 2008, he reached the final of the Canary Wharf Squash Classic, losing James Willstrop in the final 9–11, 11–9, 8–11, 11–6, 11–3.In November 2010, he won the Dutch Open against Laurens Jan Anjema in the final 11–7, 11–9, 11–13, 14–12.On 3 October 2011, Pilley hit a squash ball recorded as 175 mph, breaking the previous record set by John White by 3 miles per hour.