Inverness born left back Bob MacDonald began as an amateur with hometown club Inverness Caledonian in 1918 before moving to Second Division Tottenham Hotspur in August the following year, making his Football League debut on the last day of the 1919-20 League season at Birmingham as Tottenham were promoted as Second Division Champions. While he wouldn’t share in that silverware, a year later he was in the Tottenham FA Cup Final line up that beat Wolverhampton Wanderers 1-0 at Stamford Bridge to win the FA Cup, having established himself as the regular full back partner for Tommy Clay, playing a month later as Tottenham followed up with a 2-1 win over Burnley in the FA Charity Shield.
He also played in the 1922 FA Cup semi final as Tottenham defended the Cup as far as Hillsborough, before losing to eventual runners-up Preston North End. His Tottenham career went in to decline after he was injured at Nottingham Forest in December 1922, and he only made 19 more appearances over the following two seasons, playing his last match for Tottenham in March 1925, totalling 126 appearances for Spurs without ever scoring. In October 1927, after a trial at Heart of Midlothian, he transferred to Clapton Orient, and went on to play a further 38 matches until March 1929 after which he retired from the game.