City suffer penalty shoot-out defeat to Chesterfield

After dominating play, Jacob Wright finally put City ahead on 52 minutes with an excellent free-kick from 20 yards out.

In an almost identical free-kick 11 minutes before the full-time whistle, substitute Darren Oldaker drew Chesterfield level and in turn, took the game to penalties to see who would earn an extra point in Group G.

Oldaker, Connor Cook, Kane Drummond, and James Berry all converted from the spot whilst Jacob Wright and Will Dickson‘s missed penalties saw City fall to a shoot-out defeat. 

WHAT HAPPENED

As the sun began to set over the SMH Group Stadium, Chesterfield’s home proved an idyllic setting to host City’s first EFL Trophy Group G fixture of the 2024/25 season.

The opening 10 minutes consisted of both teams figuring out their respective game plans.

City were forced into an early change with Tai Sodje replaced by Justin Oboavwoduo in the 13th minute.

A minute later Joe Quigley looked to capitalise on a loose City pass. The forward tried to place the ball into the bottom right corner but was denied by an outstretched Jack Wint.

O’Reilly dinked the ball onto the crossbar from the left-hand corner of the Chesterfield box as gasps echoed round the stadium on 21 minutes.

Just seconds before Farid Alfa-Ruprecht was unleashed on the right flank and he showcased his lightning speed.

He tried to find Jaden Heskey in the centre of the box but his low cross flew just behind his intended target.  

On 41 minutes the hosts had their best chance of the game so far when Kane Drummond’s curled effort went inches wide of the right post.

Drummond looked to emulate his original attempt on the brink of half-time. A nutmeg on Jacob Wright opened up space in front of the City goal before Jahmai Simpson-Pusey got in front to block Drummond’s effort.

The resulting corner saw Lakyle Samuel head the ball off City’s goal line to deny Spireites captain Jamie Grimes the opener.

Wilkinson’s side held 71% possession in the first half and it was clear from as soon as the second half began they were looking to do more of the same.

The outstretched leg of skipper Grimes tripped Heskey on the edge of the box on 51 minutes with City’s high press causing Chesterfield issues and in turn Wilkinson’s side were awarded a free-kick.

Wright, with a decent track record of set-pieces for the young Blues, was the first to stand over the ball and lay claim to the free-kick - and he wouldn’t disappoint.

The 19-year-old curled the ball precisely out of reach of goalkeeper Ashton Rinaldo to put City ahead with a fantastic strike.  

But last season’s runaway National League champions were not to be denied.

The hosts were awarded a free-kick on 78 minutes in almost an identical place to where Wright’s free-kick was for City.

Substitute Oldaker curled the ball into the back of the City net, albeit against the run of play, to level the scores.

Divine Mukasa tried to stop the game from going to penalties on the brink of full-time, but his left-footed effort drifted away from the goal and in turn a penalty shoot-out would decide who gained an extra point.

Oldaker, Drummond, Cook and Berry all converted Chesterfield’s penalties. Wright and Dickson were unable to net their spot kicks and though Mukasa and O’Reilly were successful, the Blues lost out 4-2 in the shoot-out.

HOW WE LINED UP

Jack Wint was tasked with protecting City’s goal with a back four of Matty Henderson-Hall, Jahmai Simpson-Pusey, Max Alleyne and Lakyle Samuel.

Jacob Wright, Michael Okeke and Nico O’Reilly were in midfielder with Tai Sodje, Farid Alfa-Ruprecht and Jaden Heskey on hand to provide attacking threat.

CHESTERFIELD XI: Rinaldo, Horton, Grimes (C), Araujo, Jacobs (Berry 83’), Williams, Hobson (Daley-Campbell 74’), Akinola (Mohiuddin 82’), Quigley (Cook 74’), Drummond, Jones (Oldaker 74’)  

SUBS: Boot, Jessop.

CITY XI: Wint, Henderson-Hall, Simpson-Pusey, Alleyne, Samuel, Wright, Sodje (Oboavwoduo 13’), Okeke (Dickson 71’), Heskey, Nico O’Reilly, Alfa-Ruprecht (Mukasa 87’).

SUBS: Naylor, Brits, Gray, Warhurst.

WHAT IT MEANS

City pick up one point in our first EFL Trophy group game of the season.

UP NEXT

City’s Elite Development Squad will be back in Derbyshire on Friday 23 August when we take on Derby County in our latest Premier League 2 assignment.

Kick-off at the Proctor Cars Stadium is scheduled for 19:00 (UK) and will be available to watch live on CITY+.