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Osborne was drafted 4th overall in the first ever first ever NHL draft in 1963 by the New York Rangers. He however never played in the National Hockey League. Following his Ontario Hockey Association stay with the Toronto Marlboros, he joined in 1967 the Omaha Knights of the Central Hockey League. He spent the next season between the Salem Rebels of the Eastern Hockey League and the Buffalo Bisons of the American Hockey League before joining the Ontario Hockey Association Senior for the last 8 seasons of his career, playing for the Orillia Terriers, the Brantford Foresters, the Cambridge Hornets and Brantford Alexanders.