The Spireites return to the EFL Trophy, now known as the Bristol Street Motors Trophy, for the first time in six years when they welcome Manchester City U21 to the SMH Group Stadium.
In the 12 games between the two sides, in first-team competition, Chesterfield have only come away with one win – a memorable 2-1 League Cup win in 2006.
However, the Blues have also come up against the U21s just the one time.
In the 2017/18 season, Jack Lester’s side were drawn in Group F against Bradford City, Rotherham United and Manchester City U21.
The Cityzens beat Rotherham on penalties after a 1-1 draw before falling to a narrow defeat to Bradford City.
On the other hand, the Spireites lost 4-2 to the Bantams before securing a late away win against the Millers.
Rotherham, who were already eliminated, then won 3-0 in their final group game against Bradford, who were already through to the knockout stages.
Heading into the deciding game, a win for either side would secure second spot and place in round two.
Chesterfield and Manchester City U21 met at the SMH Group Stadium at the end of November 2017.
The home side had the ball in the back of the net when Andy Kellett slotted the ball beyond Aro Muric – but the linesman’s flag was up.
The Blues dominated proceedings in the first half but efforts from Chris O’Grady and Jerome Binnom-Williams failed to find the back of the net.
Half time failed to bring any rest bite to City as Chesterfield continued their control of the ball; Muric was on hand to palm away dangerous chances from O’Grady and Binnom-Williams.
Joe Rowley replaced Diego De Girolamo in the 73rd minute and it took less than a minute for the midfielder to make an impact. Binnom-Williams whipped in a cross that Rowley powerfully headed into the bottom corner to open the scoring.
Two minutes later, Charlie Oliver caught Andy Kellett with a rash challenge that gave Darren Dysdale no choice but to brandish the red card.
Despite having a man disadvantage, Manchester City found themselves level in the 88th minute – Ed Francis’ free-kick flew past a helpless Joe Anyon.
As the game ticked into added time, the away side produced a blistering counter-attack that was finished off by Lukas Nmecha.
It looked like the Spireites would fall to a late defeat, but one last chance would fall to the hosts in the seventh minute of added time. Bradley Barry’s cross ricocheted off a defender and into the path of O’Grady, who lashed home a half-volley from eight-yards.
The goal sealed Chesterfield’s path to the knockout stages however, a penalty shoot-out was needed to see who would get the extra point.
Kellett missed the first penalty before Nmecha scored to give the away side the lead. Louis Reed, Francis, Rowley, Taylor Richards and O’Grady then all scored to make it 3-3, with Manchestre City having a penalty advantage.
Demeaco Duhaney was then thwarted by Anyon to essentially send the shoot-out into sudden death. Sam Hird made it 4-3 before Tyreke Wilson struck the post to give the Blues the extra point.
The Spireites went on to face Fleetwood Town in the second round; unfortunately for Lester’s side, they would lose 2-0 to bring an end to their EFL Trophy run.
