Trained as a plumber, Hobson continued to play in local football, turning out for Sheffield Rangers on Saturdays and for Manchester Villa, a Chesterfield pub team, on Sundays.
He made his professional debut against Cambridge United in April 1978, producing "a sparkling performance in which he seemed to mesmerise the opposition defenders"[3] with his crosses from the right flank providing two goals for "the Imps" and scoring once himself in a 4–1 victory.
[4] Hobson quickly became established as a first-team regular, generally playing at outside-left with Glenn Cockerill on the right and Mick Harford in the centre.
He made his debut for "the Saints" on 29 November 1986 when he scored the final goal in a 3–1 victory, knocking in the loose ball after goalkeeper Tony Coton failed to hold a shot from Cockerill.
Graham Baker took his place in the side,[8] and by the time that he was fit again, Hobson found it hard to break back into the team, especially with the emergence of younger players such as Rod Wallace, Matthew Le Tissier and Alan Shearer.