In 2005, he was awarded the club's 'defensive pursuits player of the year'. In 2008 Osborne played in 20 of the 22 home-and-away games, and was part of Hawthorn's premiership team and finished 5th in the Peter Crimmins Medal.
In 2005, he received recognition for his defensive skills and was awarded 'defensive player of the year'. In 2008, Osborne played a key role in Hawthorn's premiership success, finishing fifth in the Peter Crimmins Medal.