Collingwood had attempted to lure the young Full-forward for years before O'Bree signed with them on match permits.
In his third game, O'Bree started well, kicking a goal then he collided with Colin Saddington, landed awkwardly and broke his right leg in a match against Richmond at their home ground Punt Road Oval.
[5] After recovering from his broken leg, O'Bree returned to play for Euroa, becoming a record goalkicker and premiership winning coach.
[5] He spent three years from 1959 as captain coach of Wycheproof in the North Central FL before returning permanently to Euroa.
He kicked 59 goals and led Euroa to the premiership before hanging up the boots for good.