The Spireites fell to a late 2-1 loss away at Solihull Moors as James Rowe tasted defeat for the first time as manager.
Rowe made one enforced change to the side that won the reverse fixture on Saturday as Josef Yarney came in for the suspended George Carline.
New loan signings Marcus Dinanga and Jack Clarke both started on the bench after signing from Aston Villa and Stevenage respectively earlier in the day.
Similar to the game at the weekend, Solihull created an early chance. Cameron Coxe made his way down the right wing before crossing the ball for Kyle Huddlin who scuffed his shot wide of the goal.
Chesterfield’s first chance of the game fell to Tom Denton who rose highest to meet Laurence Maguire’s cross, but his header was off target.
Tom Whelan, the goalscorer from the weekend, looked to make it two in two when he picked the ball up just inside the home side’s half. The midfielder ran towards the 18-yard box before firing an effort that forced Ryan Boot into making a save.
In the 36th minute, the Spireites took the lead. Jak McCourt’s corner found Denton at the far post and the forward headed home for his ninth goal of the season.
Before the break, Whelan missed a great chance to double the lead. A cross caused havoc in the penalty area before the 22-year-old blasted the ball over from close-range.
The second half started with a sustained period of possession from the hosts. Justin Donawa met a cross on the half-volley and his effort flew just over the crossbar.
Just before the hour-mark, Akwasi Asante almost pulled out a screamer of a goal. The striker picked up the ball 30 yards from goal before passing five defenders with a mazy run before striking the upright.
Two minutes later, Solihull Moors found an equaliser. Donawa rose highest from a cross which Kyle Letheren did very well to save. Unfortunately, Joe Sbarra was first to react and tapped home from close-range.
The Spireites looked to retake the lead and came close twice. Curtis Weston latched onto substitute Dinanga’s pass, but Boot made a smart save. The midfielder picked the ball back up but his goalbound effort was blocked and cleared away.
Asante had a shot of his own soon after, but it was deflected out for a corner. From the set-piece, Yarney hooked the ball towards goal and the ball was cleared on the goalline.
The home side scored a late winner three minutes into stoppage time. Jamie Ward’s cross found Huddlin who headed home with the ball just squirming under Letheren.
Chesterfield: Letheren, Yarney, Evans, Hollis, Maguire, Taylor, Weston, McCourt, Whelan (Mandeville 55), Tom Denton (Dinanga 59), Asante.
Unused Substitutes: Cropper, Smith, Clarke