Hutchinson holds the distinction of winning the most races in a single Isle of Man TT meeting, when he achieved a clean sweep of five solo wins in 2010.
Hutchinson made his debut on the Island at the 2003 Manx Grand Prix, winning the Newcomers race on a 600cc Honda, beating the 750cc Suzukis of Jonathan Ralph and Alex Donaldson.
The 2004 North West 200 was a nightmare for Hutchinson, as within yards of starting his first practice lap of the circuit, he injured his leg and put himself out of the meeting. Hutchinson made his Isle of Man TT debut in 2004, competing in four races all on board a Suzuki. Despite recording the eighth fastest lap in the final Junior TT practice session, Hutchinson would only take one top ten finish in the Formula One TT, edging out Manx rider Gary Carswell by 2.3 seconds after 150 miles racing. He also competed in selected races of the British Superstock Championship. He returned to the Isle of Man in 2005, but this time campaigned Hondas throughout the races. After making the top five in Superstock practice, Hutchinson ended the week with three top tens and an eleventh place finish. He also made his debut at the Ulster Grand Prix in 2005 and continued with selected British Superstock races.