Harry James Osman (29 January 1911 – 17 December 1998) was an English footballer who played as an outside left for Southampton for two seasons in the 1930s and went on to become manager of Winchester City where he "discovered" future England international Terry Paine.
Osman moved back to Hampshire on a free transfer,[2] making his debut for Southampton (in the Football League Second Division) on 28 August 1937, the first day of the 1937–38 season.
Unable to find the exciting form of the previous season, Osman managed only nine goals (from 30 appearances) before he was sold to Second Division rivals Millwall in March 1939 for a fee of £2,000,[2] a move that came as a shock to the Southampton fans, although, in hindsight, this turned out to be a very good piece of business.
He returned to The Dell as a guest player in War Leagues in 1939–40, before joining the Tank Corps where he was wounded while serving in Italy.
[4] After retiring from football management in October 1957, Osman emigrated to Palm Beach, Florida where he died on 17 December 1998.