The Spireites fell to a 2-1 defeat to Maidenhead United at the Technique Stadium, after leading through Scott Boden’s first-half volley.
John Pemberton made three changes with Jordan Cropper, Joe Rowley and Boden all returning to the starting line-up.
The visitors came close to opening the scoring in the first couple of minutes. Ryan Upward picked up the ball in the box from a Maidenhead cross before rolling his effort wide of the post.
Two minutes later, Cropper was allowed to launch one of his long throws into the area. The set-piece caused problems and was deflected wide and out for a corner.
Chesterfield were inches away from taking the lead through Laurence Maguire; Tom Denton powered a header from David Buchanan’s cross over to the defender but his header from point-blank range rattled the upright.
On the half-hour mark, the Spireites took the lead. Kyle Letheren’s long goal kick found Boden just outside the box and the striker volleyed the ball over Taye Ashby-Hammond’s head for his first goal of the season.
Maidenhead almost went into the break level. Many Parry rose highest from a corner, his header had Letheren rooted to the spot, but the ball bounced wide of the mark.
A frantic start to the second half saw both side close to grabbing an early goal. Firstly, a miscommunication allowed Boden to pick the ball up in the area, but his goalbound effort was cleared off the line.
Just a minute later, the away side came close themselves. Nathan Blissett managed to turn Maguire in the area, but Letheren was quickly out to deny the forward.
However, the away side found an equaliser in the 55th minute. Sam Barratt floated a cross into the Chesterfield penalty are which somehow found a way into the back of the net.
The Spireites came so close to retaking the lead through an unlikely source when Buchanan lined up a volley to meet Curtis Weston’s header, but his attempt crashed off the right-hand post.
With 20 minutes to go, the visitors took the lead. An in-swinging corner from Josh Coley found the head of Barratt, who headed home from a tight angle.
Chesterfield threw everything at the Maidenhead defence in search for an equaliser. Cropper burst forward and fired a shot at goal, but his attempt hit the side-netting.
The full-time whistle followed soon after. The Spireites’ next National League game is away at Altrincham on Tuesday.
Chesterfield: Letheren, Cropper, Sharman (Rawson 78), Evans, Maguire, Buchanan, Butterfield, Weston, Rowley (Kiwomya 89), Boden, Tom Denton.
Unused Substitutes: Wharton, Hollis, Smith.