The Spireites have qualified for the knockout round of the Vertu Trophy after a 2-2 draw against Liverpool U21s at the SMH Group Stadium on Tuesday evening.
Goals from Bailey Hobson and Dylan Duffy had given Chesterfield a commanding 2-0 lead, until Kaide Gordon’s late double sent the game to a penalty shoot-out.
The visitors ultimately came out on top from the spot after a marathon shoot-out that ended 11-10.
After Burton Albion’s defeat against Crewe Alexandra, it meant that Chesterfield finished second in Northern Group H.
Paul Cook made wholesale changes to the side that drew 3-3 against Accrington Stanley on Saturday, with only Tom Naylor and Liam Mandeville retaining their place in the starting XI.
It was a positive start from the home side, with Duffy causing early problems for Calvin Ramsay.
Ramsay, the Liverpool captain for the evening, was into the book after just four minutes with a frustrated pullback on Duffy.
The visitors put together their first real attack of note after a mazy run from Gordon, but Joseph Bradshaw couldn’t direct his header goalward.
Bradshaw had another opportunity when the forward beat the offside trap; however, his first effort was stopped by Ryan Boot, and his follow-up found the roof of the net.
Boot was tested again moments later, this time by Gordon, whose curling effort was palmed away by the shot-stopper.
Chesterfield came out after the break on the front foot, though the Spireites were still to test Fabian Mrozek.
Finally, with 62 minutes played, Chesterfield found the breakthrough.
Hobson’s low strike skidded across the slick surface and underneath Mrozek to make it 1-0.
Two minutes later, the Spireites doubled their advantage.
Duffy, who had been the bright spark all game, cut inside and curled his effort into the top right corner.
It was all one-way traffic from this point as Ronan Darcy and John Fleck both had chances to make it three.
Substitute Josh Sonni-Lambie spurned a chance to get Liverpool back into the game when putting his effort wide when one-on-one.
However, in the 76th minute, Liverpool did get a goal back.
After a loose Jamie Grimes back pass, Sonni-Lambie this time opted to square the ball to Gordon, who finished clinically.
As the game looked to be heading for a Chesterfield win, Gordon struck again in stoppage time.
With a similar finish to his first, the Liverpool forward took the game to a penalty shoot-out.
After a marathon shoot-out, Liverpool ultimately proved victorious, winning 11-10 after Fleck crashed his second effort against the bar.
Chesterfield: Boot, Tanton (Daley-Campbell 77), Donacien, Grimes, Sheckleford, Naylor (Fleck 46), Mandeville (Cook 68), Hobson (Berry 77), Duffy (Markanday 77), Darcy, Dickson
Attendance: 2,631
