 Osbourne joined Leeds United on trial in July and he played for Leeds in friendlies against Rochdale and Sheffield Wednesday.But was unable to earn a permanent deal.Osbourne signed with Hibernian, and he soon agreed a two-year contract with the Scottish Premier League club.Osbourne made his Hibernian début on 14 August 2011 in a 4–1 away loss at Kilmarnock, coming off the bench at half-time to replace Lewis Stevenson.