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Bo’ness, Lothian born outside left Bert Oswald began his football career with Linlithgow Rose, from where he was signed by Scottish First Division club Heart of Midlothian in November 1924, making his Scottish League debut, and only appearance for The Jambos, in a 1-0 win over Aberdeen at Tynecastle in September 1925. He was sold to East Stirlingshire in October 1925 and moved on to hometown club Bo’ness in February 1926, from where he was signed by Second Division club Reading in June 1928, making his Football League debut against Middlesbrough that August. A near ever present at Reading, missing just one match a season in each of his two seasons at Elm Park, he scored 16 goals in 85 matches for The Royals before being signed by First Division club Sheffield United in July 1930, who paid Reading £4,000 to take Oswald and Percy Thorpe to Bramall Lane.
Initially he struggled to establish himself in The Blades’ first eleven, but from October 1931 he was a regular, missing only one match in their 1932-33 campaign. However after their relegation in 1934 he was transferred to Third Division (South) club Southend United for £500 after 24 goals in 111 matches for Sheffield United. He had five seasons with The Shrimpers and by the time of the outbreak of the Second World War in September 1939, which effectively ended his career, he had scored 23 goals in 137 matches for Southend United.
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