John started his football career as a half-back with his school and junior sides but had converted to keeping goal by the time he turned professional with the Spireites, thirteen months after first joining the club.That didn't stop him taking the field with the number 9 on his back, once, against Crewe at Saltergate in '65-6.Tony McShane's resources had been stretched wafer-thin and, in the previous game, he had tried Albert Holmes at centre-forward after losing Ivan Hollett to injury. Although John didn't complete the fairy tale by scoring, Town won 3-1 and Crewe's Keith Stott, marking Osborne at centre-half, was forced to put through his own net. McShane's experiment may have been a qualified success, then, but it was never repeated.
An alert 'keeper, with good positional sense, John became famous for bravery that indicated little regard for his own well-being.He was also involved in some moments that might be put down to goalkeeping eccentricity and that led to the club conceding bizarre goals, such as the fifty-yarder from Sammy Chapman against Mansfield in September, '62. Consequently, perhaps, the club never quite realised John's true worth, and when he joined the Baggies in 1967, it was for a comparatively small fee, in the light of his contribution to them.
At the Hawthorns, John won an FA Cup winner's medal at the end of his first season. A measure of the regard in which he came to be held can be taken from the fact that his 1978 testimonial raised £32,000, which was a record for the Baggies at that time. A keen ornothologist and cricketer, Ossie once ran a sportswear business with the former Villa 'keeper Jimmy Cumbes, and was the Commercial Manager for Worcestershire County Cricket Club; John ran his own Worcester-based business until his untimely death from cancer at the age of 57.
For Chesterfield: 110 Football League appearances. 29 clean sheets, 159 conceded.