[1] Its first team joined and won the Sheffield & District League in 1891–92,[2] and first entered the FA Cup the following season.
Drawn away to Gainsborough Trinity in the first qualifying round, the score stood at 2–2 at full time; Trinity scored twice during extra time, but darkness fell before the agreed half hour was complete, so the match was ordered to be replayed.
They won the first post-war Midland League title[1] – and were expelled from that season's FA Cup for fielding an ineligible player[a] – but when the football authorities made clear their opposition to municipal ownership of clubs, the council's involvement ceased and the club was renamed Chesterfield F.C.
In 1980–81, they entered and won the last edition of the Anglo-Scottish Cup, defeating Scottish giants Rangers 3–0 in the quarter-finals before beating Notts County in the final.
[5] Two years later, they were relegated, and came close to folding, with debts of £400,000 and only seven contracted professionals,[6] before bouncing back to win their second Fourth Division title in 1985.
With 21 minutes left and Chesterfield leading 2–1, Jonathan Howard shot against the underside of the bar; the ball bounced down and then out, and referee David Elleray ruled, incorrectly, that it had not crossed the line.
Middlesbrough scored, and took a 3–2 lead in extra time, but Jamie Hewitt equalised with seconds left.
[7][8] In 2000–01, a nine-point deduction for financial irregularities, initially deemed too lenient by the Football League, failed to prevent Chesterfield's automatic promotion in third place,[9] and the following year the club was taken out of administration into the ownership and control of the Chesterfield Football Supporters' Society.