Osborne has won two PDC Pro Tour events and he also managed to hit two perfect nine-dart finishes in 2005.
Osborne suffered a surprising first round exit in the 2008 World Championship, losing 3–1 to Dutchman Erwin Extercatte.
Having beaten Raymond van Barneveld, Jamie Caven and Kevin Painter in the earlier rounds, he lost 11–6 to Taylor in the final.
He also won the 2009 Championship League Darts, defeating Taylor 6–4 in the final, but a disappointing year in the other majors was compounded with a first-round loss to Simon Whitlock in the 2010 World Championship, a match that was dubbed "The Battle of the Wizards" due to both players being nicknamed 'The Wizard'.
At the Grand Slam of Darts, Osborne lost his opening group match to Robert Thornton before beating Whitlock and Dave Chisnall to qualify for the knockout stages.