Chesterfield progressed to the knock-out stages of the Checkatrade Trophy after a Sam Hird spot kick sealed a 4-3 penalty shoot-out win against Manchester City U21s after the match finished 2-2 at the end of 90 minutes.
The first chance of the game fell to the visitors when Javairo Dilrosun made a good run down the right and cut inside onto his left foot before putting his effort over the bar.
Chris O’Grady then put Andy Kellett through on the left and he tried to loop the ball over Aro Muric, but his effort landed on the roof of the net.
Dilrosun continued to pose a threat. Cutting in from the right again, he took aim, only to see his well-struck effort sail over the bar.
The Spireites had the ball in the net when O’Grady turned and had his shot well blocked only for the ball to fall to Kellett who found the net from six yards out, only to be ruled off-side.
Kellett was again sent down the left-hand side and found O’Grady, whose effort was saved by Arijanet Muric.
Only a few minutes later, the Spireites had an even better chance when Jerome Binnom-Williams rose the highest to meet a corner ball, but despite making good contact, he put his header wide.
With half time approaching, the Spireites pushed for the lead. Kellett was almost sent clean through after a long ball over the top, only for the referee to penalise O’Grady for bringing down defender Charlie Oliver in the build-up.
One minute before half-time, it was Jak McCourt’s turn to have a shot. Receiving the ball on the left flank, he let fly, only to see his curling effort go narrowly past the upright.
After a quiet start to the second half, Binnom-Williams burst into the box from the left and shot from a narrow angle, forcing Muric into a good save.
Little over a minute later, Muric was called upon again, touching wide a good long-range effort from O’Grady.
City appealed for a penalty when Lukas Nmecha went down inside the area after being put clean through on goal, one-on-one with Joe Anyon.
Joe Rowley replaced Diego De Girolamo in the 72nd minute and he made an instant impact. After a great passing move on the left, Binnom-Williams floated a terrific cross into the box to find Rowley, who expertly aimed his header down low into the corner of the net to put the Spireites a goal up.
Little over a minute later, the Spireites were also a man up. In a 50/50 challenge, Oliver crashed into Kellett with his studs raised, forcing the referee to issue a straight red card.
A second goal would’ve meant the Spireites topping the group. Trying to grab a second, Binnom-Williams made another great run into the City’s box and forced Muric into another good save.
Rowley had another chance to add to his tally. However, after wriggling free deep inside the box, he could only put the ball straight at Muric.
Four minutes from time, City snatched an equaliser thanks to a brilliant free-kick from Ed Francis. Twenty yards out, he curled the ball into the net with Anyon rooted to the spot.
Two minutes later, City snatched the lead, A quick breakaway into the box ended with Lukas Nmecha making no mistake, guiding the ball past Anyon.
Deep into stoppage time, O’Grady nearly grabbed an equaliser when his header forced Muric to make an excellent save down low to his left.
Little over a minute later, O’Grady made no mistake when fired past Muric after meeting Bradley Barry's cross.
That set up a penalty shoot-out. O’Grady, Rowley and Reed and converted for the Spireites and Nmecha, Ed Francis and Taylor Richards scored for City. Then Demeaco Duhaney stepped up and his weak effort was saved by Anyon.
Tyreke Wilson then dragged his effort well wide of the target and up stepped Sam Hird, who sent Muric the wrong way, slotting the ball into the bottom corner of the net.
The Spireites will now travel to Fleetwood Town next Tuesday night.
Chesterfield: Anyon, Barry, Hird (C), Maguire, Binnom-Williams, Reed, McCourt (Weir 57'), Dimaio (Wakefield 85'), De Girolamo (Rowley 72'), O'Grady, Kellett.
Substitutes: Parkin (gk), Wiseman, Dennis, Briggs
Manchester City U21s: Muric, Duhaney, Wilson, Oliver, Francis, Davenport, Dele-Bishiru, Smith (Richards 69'), Nmecha (C), Diloruson (Diallo 80'), Garre (Gonzalez 63').
Substitutes not used: Sokol (gk), Latibeaudiere.