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Dundee born centre forward or inside right Willie Oswald began his football career with Dundee Celtic in 1920, and played as a trialist of Dundee Hibernian (United as is today) in April 1922, scoring twice in a Scottish League Second Division 4-1 victory over Armadale. However he chose instead to head to English football and joined Gillingham over the close season, making his Football League debut at Northampton Town the same August. He scored 3 times in 13 appearances during 1922-23 before returning to Scotland to join St Johnstone in the summer of 1923. He then re-joined Dundee United (by now re-named) the following close season, scoring 17 goals in 52 appearances over the next two seasons, scoring 12 goals as they won the 1925 Scottish Second Division Championship to enter the top flight for the first time in the club’s history.
Having been released by United at the end of the 1926 campaign, he returned south and joined Brighton & Hove Albion, where he was mainly a fringe player scoring twice in 14 appearances between March 1927 and February 1928. He then joined many players of the time by crossing the Atlantic to join the nascent American Soccer Leagues, playing for Providence Gold Bugs from 1928, and subsequently both Fall River and New York Yankees in 1931.
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