A strong muscular centre half (in those days the centre half played in midfield), Dick immediately made his debut for Arsenal on the first day of the season (against Luton Town on 3 September 1898), and he only missed four games of his first season.
Dick was noted for his formidable stamina (he was a cross-country runner as well and once recorded a time of six-and-a-half miles in 33 minutes, 45 seconds), and was a near ever-present in the Woolwich Arsenal side for the next six seasons; he missed only one game in 1899–1900, and although not a prolific goalscorer (he only scored thirteen times in his entire Arsenal career), he did score twice in a 12-0 demolition of Loughborough on 12 March 1900, Arsenal's record win in a competitive match.
In the meantime he had also become club captain, though by the time promotion had come round, fellow Scot Jimmy Jackson had taken over as skipper.
During this season he played one game for Crystal Palace, on the 17 April 1906 in the Southern Football League Division Two.
In the summer of 1912 he left Arsenal to coach abroad in Prague, and became known for being one of the early pioneers of football in Czechoslovakia, where he successfully coached DFC Prag and Sparta Prague[4] (at that time another Scot, Jake Madden, was in charge of Sparta's city rivals Slavia).