Stephenson fell one game short of qualifying for the 2007 PDC World Darts Championship, losing to Alan Tabern. He then fell two rounds short in qualifying for the 2008 PDC World Darts Championship, losing to Kirk Shepherd who eventually qualified and went on to reach the final. Stephenson finally qualified for the World Championship at the third time of asking, beating Jason Clark, Gary Welding and then Ray Farrell to earn one of the eight qualifying spots. He faced five-time world champion and the number 2 seed Raymond van Barneveld in the first round, losing 3 sets to nil.