 He made his Premier League debut on 21 October 2006, when he came on as a substitute in the 83rd minute for Steven Davis against Fulham at Villa Park.28 December 2006 saw Osbourne sign a new three-and-a-half-year contract, keeping him at Villa Park until the summer of 2010.On 10 January 2008, Osbourne agreed to join Ian Holloway's Leicester City on loan, however just a few days later Villa manager Martin O'Neill was forced to cancel the proposed deal because of mounting injury concerns.