A ball winning midfielder, he won an AFL Rising Star nomination in the first week of 1999, having 27 touches.
Collingwood coach, Michael Malthouse, was very interested in O'Bree due to his brilliant display in his second AFL season.
Steady seasons in both 2004 and 2005 kept him going, despite his lack of speed in a slow midfield outfit, he still found the ball and tackled hard.
After retiring as a player, he joined the Gold Coast Suns as a midfield assistant coach for their inaugural season in the AFL in 2011.
[2] At the end of the 2012 season, O'Bree moved back to Victoria and joined the Geelong Football Club as a midfield stoppage assistant coach.