Chesterfield 2 Manchester City 1: Niven plays a leading role to heap pressure on Pearce

Manchester City's year of discontent plumbed fresh depths last night when they suffered another of their notorious cup calamities.

Chesterfield, who are languishing in 17th in League One, came from behind to take their first ever top-flight League Cup scalp and savour their finest hour since reaching the semi-final of the 1996-97 FA Cup.

What is more, they deserved it, although the 67th-minute winner from their midfielder, Derek Niven, was the sort dreams are made of.

Stuart Pearce could be in trouble if the current round of manager sacking spreads to the Premiership. City have now lost three games in a row, and 11 of their last 12 Premiership trips, and at times lacked the necessary appetite for such an earthy battle.

"We should have gone on and won, and I'm bitterly disappointed," Pearce said. "We have to take a close look at ourselves and work even harder, but I don't want to take anything away from Chesterfield. Good luck to them."

City started at a gallop, with Georgios Samaras twice and Bernardo Corradi going close before Samaras drove in a rebound after his strike partner had headed Micah Richards' 40th-minute centre against the inside of the post.

Chesterfield were on top by then, though, with Caleb Folan spooning over from a one-two with Niven.

Only six minutes of the second half had elapsed when the shaky Nicky Weaver misjudged his advance to Kevan Hurst's free-kick and left Folan to head home.

Chesterfield were sufficiently galvanised to go and add their name to those of Doncaster Rovers and Oldham Athletic from City's nightmare recent cup past.

Phil Picken's left-wing centre was headed out, but Niven lashed in a magnificent first-time right-foot shot from almost 25 yards.

"Over the 90 minutes, I honestly thought we were the better side," said the Chesterfield manager, Roy McFarlane. "We have made a bit of history, and that winner would grace any game. I feel for Stuart. He is at a big club and has to turn it round, which I think he will."

Chesterfield (4-4-2): Roche; Bailey, Downes, Hazell, Picken; Hall, Niven, Allott, Hurst; Shaw (Allison, 78), Folan. Substitutes not used: Jordan (GK), Jackson, Larkin, O'Hare.

Manchester City (4-4-2): Weaver; Richards, Dunne, Distin, Jordan (Dickov, 84); Sinclair, Barton, Hamann (Ireland, 78), Reyna (Miller, 71); Corradi, Samaras. Substitutes not used: Hart (GK), Beasley.

Referee: K Wright (Cambridgeshire).