The Spireites fell to their first home defeat of the season, losing 3-2 against Solihull Moors at the Technique Stadium.
After a bright start the Spireites fell away, letting slip a two-goal lead.
The Spireites were under pressure in the first ten minutes of the game, struggling to get the ball out of their half.
Against the run of play, the Spireites took the lead in the 14thminute. Alex Whittle struck the ball into the bottom right of the net, with a deflected effort from around six yards out.
Akwasi Asante doubled the lead 21 minutes in. Liam Mandeville tried his luck from range, the keeper parried it away, Asante picked up the loose ball on the edge of the box and fired into the bottom left corner.
Captain Curtis Weston was dismissed in the 22nd minute for violent conduct.
Solihull Moors grabbed a goal back in the 37th minute. James Clarke met the ball with his head at the back post, beating Scott Loach.
Jak McCourt cleared the ball off the line from Andrew Dallas.
The Spireites went into half time with a 2-1 lead.
Solihull’s Callum Maycook should have levelled the scores after the ball was squared to him, but he slipped and missed what was virtually an open net.
However, Maycook did level in the 51st minute when the ball was pulled back to him on the penalty spot and he drilled past Loach.
Solihull took the lead in the 55th minute after the ball was laid off to Harry Boyes from an indirect free kick on the edge of the six-yard box. He drilled the ball through the wall of Chesterfield players.
Loach produced a great save in the 71st minutes, denying Maycook in a one-on-one situation.
Once again Loach kept Chesterfield in the game with an excellent save from Dallas’ attempt just inside the box.
Chesterfield were down to nine men in the closing minutes of the game after McCourt was taken off on a stretcher.
Saidou Khan dragged a shot wide in added time.
Loach made another terrific save late in added time, tipping the ball over the bar from Boyes’ attempt.
The Spireites will now look towards Tuesday’s home game against Wrexham.
Spireites: Loach, Williams, Kerr (Whelan 69’), Grimes, Kellermann (Miller 81’), Weston, McCourt, Whittle, Mandeville, Quigley (Khan 72’), Asante
Subs: Maguire, Denton
Attendance: 7,391 (182 away)