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Scottish goalkeeper Harry McGregor was playing for East Stirlingshire before signing for Dundee United after showing up well in a public trial in August 1928. He made his debut at the beginning of September 1928 against Dunfermline Athletic, displacing Jock McHugh between the posts. He became the first choice keeper for the rest of the season and helped the side to promotion, playing 37 times, winning the Scottish Second Division Championship. During the First Division campaign that followed, McGregor became the understudy to McHugh making only 12 more appearances until the end of the season and was released in April 1930, joining Alloa Athletic.
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