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Dundee born outside right Mitchell “Mickey” McGregor began his football career with Dundee Stobswell from where he joined hometown Scottish First Division club Dundee United in March 1926, making his Scottish League debut in a 3-1 victory at Raith Rovers the same month, his only appearance of the 1925-26 season. He became a regular over the following two seasons, and despite their relegation in 1927 he stayed a further season in the Second Division. He was released in April 1928 and joined Montrose after 12 goals in 71 appearances for The Terrors.
McGregor then moved to Arbroath in February 1929 for whom he scored 3 goals in 12 appearances for the Gayfield club before they transferred him to First Division club Falkirk in September 1929. In 1930 it was said of him “Playing alongside the famous “Patsy” Gallagher, McGregor has come on quickly since joining Falkirk and should he in the running for honours.” His spell at Falkirk ended in 1931 when he moved south to join Southern League club Dartford, and he was part of their team that won the Southern League Eastern section title in 1931-32 and the overall Championship of the League was won with victories over the Western Section winners Exeter City Reserves 7-2 away and Yeovil & Petters United 2-1 at home respectively, also helping them to win the Kent Senior Cup in 1932, 1933 and 1935.
In addition Dartford gained a reputation nationally by becoming the first club outside the Football League to reach the FA Cup Third Round Proper in successive seasons. In January 1936 McGregor played on the right wing as Dartford lost 3-2 to a star-studded Derby County (then second in the First Division) at The Baseball Ground having at one time led by 2-0. They previously had beaten Cardiff City 3-0 and Gainsborough Trinity 4-0 to reach the Third Round, after which leading player Fred Dell was transferred to West Ham United for a reported £2,000 immediately after the game. The following season saw Dartford lose 1-0 at home to Darlington at the same stage with McGregor again in Dartford’s team, The Darts having beaten both Peterborough United and Shildon 3-0 in the earlier rounds to get there. McGregor continued to play for Dartford throughout most of the rest of the 1930’s before his eventual retirement
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