The Blues need a win to progress to the next round and thought it had been earned in the most dramatic of fashions as Lukas Nmecha scored in the final two minutes to put them ahead.
Chesterfield’s Joe Rowley had opened the scoring in the 74th minute before Charlie Oliver was sent off and during a period of eight minutes added time, the home side capitalised on their one-man advantage through Chris O’Grady.
The draw sealed City’s fate, though a penalty shoot-out followed and it was Chesterfield who emerged victorious after Demeaco Duhaney and Tyreke Wilson missed for the Blues.
What happened
It was a first half in which the driving runs of Javairo Dilrosun produced the most eye-catching action, but with few clear-cut chances.
The Dutch winger conjured up the first effort of the match as he drove inside from the right flank onto his favoured left foot and fired over the bar from 10 yards.
City looked assured in the opening period and were dictating the flow of the game with the midfield trio of Jacob Davenport, Matt Smith and Tom Dele-Bashiru finding maroon shirts with ease.
Dilrosun was proving an effective outlet and he went close again in the 12th minute as he surged through the centre of the pitch and sent one over the bar from 25 yards.
Chesterfield responded after City’s early dominance and went close three times in six minutes.
The tricky Andy Kellett thought he’d scored as he reacted quickest to a ball ricocheting around the penalty area and slotted past Aro Muric, but the assistant referee judged him to be offside.
He then turned provider as his centre was met by the toe of O’Grady.
It was the slightest of touches from the centre-forward and the ball looked to be heading for the bottom corner but Muric showed great reflexes to keep it out.
A minute later and Jerome Binnom-Williams could have scored for the hosts as he rose highest at a corner, but his header flashed past the left-hand post.
City responded and Nmecha kept the Spireites’ defence occupied, but the final ball was lacking and the two sides headed into the break goalless.
The home side took control of the game early in the second period and enjoyed their best spell of possession up to the hour mark.
Muric was called into action in the 65th minute as Binnom-Williams slalomed his way in the area and unleashed a shot from the left and the young ‘keeper produced another good save shortly after to palm away O’Grady’s curling effort.
Lorenzo Gonzalez was introduced as Simon Davies’ side went in search of a breakthrough and it nearly came courtesy of Nmecha.
Stealing the ball 30 yards from goal he powered into the area and collided with Chesterfield ‘keeper Joe Anyon as he was about to pull the trigger, but referee Darren Drysdale waved away the penalty appeals.
The introduction of Rowley for the home side saw the game spring to life as he gave the League 2 outfit the lead 16 minutes from time.
Binnom-Williams picked him out at the far post and the striker sent his header into the bottom left corner.
City’s hopes of an equaliser were dented two minutes later as Oliver’s halfway line tackle on Kellett earned him a red card and the deficit might have increased if not for Muric, who again denied Binnom-Williams in the six-yard box.
But the Blues weren’t done and they equalised in fine fashion in the 88th minute after Nmecha was fouled 25 yards from goal.
Ed Francis stepped up and curled a wonderful effort into the top right corner.
And City were ahead two minutes later as Gonzalez’ right wing run allowed him to flash the ball across the face of goal with Nmecha there to turn it home from six yards.
It was a goal that would have sent City through to the next round, but with eight additional minutes a frantic finale beckoned and they were forced to play with nine men as Dele-Bashiru limped off after all three substitutions had been made.
Chesterfield made their numerical advantage pay as O’Grady powered home Bradley Barry’s right-wing cross to equalise deep into added time.
The goal sealed City’s fate but competition rules dictate that games level after 90 minutes must go to penalties, with a bonus point up for grabs for the winner.
Nmecha, Francis and Taylor Richards all scored for City, but Duhaney saw his effort saved and Wilson fired wide, giving the Spireites a 4-3 shoot-out victory.
How they lined up
Davies made three changes to the team that lost to Bradford City in the same competition in October, with Davenport, Dilrosun and Nmecha coming into replace Richards, Rabbi Matondo and Gonzalez respectively.
The back five remained the same, with Muric protected by Duhaney, Oliver, Francis and Wilson.
Davenport was alongside Smith and Dele-Bashiru in midfield, with Dilrosun and Benjamin Garre either side of Nmecha.
Up next
A UEFA Youth League trip to Shakhtar Donetsk beckons, with the U19 squad heading out Ukraine on Wednesday 6 December knowing a spot in the last 16 is already secured.
Domestic action returns four days later as the EDS welcome Arsenal to the Academy Stadium.
