The Spireites were forced to settle for a 2-2 draw with Stockport County at Edgeley Park after holding a two-goal lead at the break.
Goals from Kabongo Tshimanga and Akwasi Asante gave Danny Webb’s side a 2-0 lead after 21 minutes.
However, a Jeff King red card early in the second half signalled the start of a Stockport comeback with goals from Will Collar and Ryan Croasdale bringing them level.
Only one change was made from the win over Dagenham & Redbridge on Saturday with Manny Oyeleke coming in for Saidou Khan.
The Blues started off well and looked to claim an early goal. King saw a tame header go wide of the mark and Tshimanga had an effort blocked at the last by Liam Hogan.
Chesterfield finally drew first blood after 16 minutes. Oyeleke played a delightful, chipped ball into the area where Tshimanga controlled with his chest before lashing a volley past Ben Hinchliffe.
Asante soon increased the lead to two goals; the striker received a long ball from Scott Loach just outside the Stockport area and saw his low drive deflected into the bottom-left corner to once again send those 2,000 fans behind the goal into delirium.
A scrappy game started to swing the way of the hosts as they aimed to find a way back into the game.
Ash Palmer rose highest to meet a corner and his header looked to have beaten Loach in the Chesterfield goal. However, referee Scott Tallis ruled that the ball had not crossed the line.
The home supporters continued to raise the noise to inspire their players, but the visitors kept a tight backline and went into the break with the two-goal lead.
Just five minutes into the second half, the first big refereeing decision was made. King went in strong on Ryan Rydel and the tackle was deemed to be a straight red card.
Stockport made that man advantage count almost straight away. Collar sent a curling effort emphatically past Loach to finely poise the game with 35 minutes left.
The home side soon found themselves on level terms as Croasdale’s 25-yard piledriver skidded across the floor and into the back of the net.
Waves and waves of Stockport attacks continued to come towards the Blues’ goal, but Ollie Crankshaw and Collar couldn’t divert their efforts goalwards.
The Spireites were dealt another blow late on when captain Luke Croll went down with a serious looking injury.
However, Webb’s men continued to stand firm and after 10 minutes of added time, were granted a point for their unbelievable efforts.
Spireites: Loach; Kerr, Grimes, Croll © (Miller 87); King, Oyeleke (Kellermann 70), McCourt, Whittle; Mandeville; Asante (Williams 54), Tshimanga.
Unused substitutes: Khan, Quigley.