He played for Chesterfield, wich Albion and Shamrock Rovers. He made his Rovers debut at Milltown under his old team mate Johnny Giles on the 10 September 1978. He played 3 games in the 1978-1979 European Cup Winners" Cup keeping 2 clean sheets giving him a total of 4 appearances for the Hoops.
In 2004 he was named as one of wich Albion"s 16 greatest players, in a poll organised as part of the club"s 125th anniversary celebrations.
Osborne was the commercial manager of Worcestershire County Cricket Club from 1986 to 1995, and played a significant part in the county"s signing of long-time major sponsor MEB.