2009 was a breakthrough year for Osborne, as he reached his first major final in the 2009 UK Open. 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'.