The Spireites’ winless streak now stands at 10 games after another desperately disappointing defeat at the Proact.
Maidenhead United were 3-1 victors and the beneficiaries of some calamitous defending.
Chesterfield had plenty of possession throughout the fixture and having fought back to 2-1 looked intent on rescuing a point, before a goalkeeping error gifted the three points to the visitors.
Once again the atmosphere soured at the Proact, with home fans chanting ‘you don’t know what you’re doing’ at boss Martin Allen when he replaced goalscorer Marc-Antoine Fortune.
The result leaves Town perilously close to the drop zone in the National League and heaps pressure on the manager.
Chesterfield took just 38 seconds to fashion a shooting chance, Charlie Carter teeing up Robbie Weir whose 25 yard effort was straight forward for Carl Pentney, but brought ironic cheers from home fans.
Within seven minutes, Town were behind, in both calamitous and unfortunate circumstances.
Weir stepped up into the play to try and intercept, the ball was passed around him and Maidenhead were away through the middle, Jerome Binnom-Williams’ last ditch tackle only succeeding in injurying his own keeper, leaving Herson Alves to find an empty net.
An apparent handball in the build up wasn’t spotted by the officials, only increasing home frustration.
The Spireites were handed multiple opportunities to deliver the ball into the Maidenhead box, thanks to persistent fouls, but the desperately poor quality of the set-pieces let the visitors off the hook.
Jordan Archer was one of those repeatedly fouling his markers, on one occasion leaving Binnom-Williams prone after an aerial challenge, but he escaped booking until the 36th minute when another foul in the air on Laurence Maguire finally brought action from ref Andrew Miller.
Chesterfield grew into the half and had little trouble dominating possession, they just couldn’t break down a stubborn defence.
When the ball did finally arrive in the area, albeit with a little fortune, Charlie Carter drove it low and goalwards only for Carl Pentney to save with a strong right hand.
Just when Town appeared on top, they conceded a second against the run of play.
Weir went into a strong 50:50 on halfway but lost out and was left in a heap as Maidenhead broke, Alves getting in behind the defence, taking it round Jalal and rolling it home.
The Spireites, who brought on Joshua Kayode for the injured Weir at the break, began the second half with plenty of intent, forcing Maidenhead into repeated fouls and a number of cautions - but still Town couldn’t create a clear cut chance.
Instead, it was Maidenhead who should have found the net, breaking through Archer who had only Jalal to beat but couldn’t hit the target.
Sam Muggleton took the place of Jonathan Smith and within seconds clipped the top of the crossbar with a cross-cum-shot.
The goal the hosts so desperately needed arrived on 67 minutes, Denton dragged to the floor inside the area by Ayo Obileye for a spot-kick Marc-Antoine Fortune slammed into the bottom right hand corner.
But disaster was to strike within two minutes, Town keeper Jalal letting a routine catch slip through his hands and rebound off his knees to Ryan Upward, who gratefully found the back of the net.
Chesterfield seemed to shrug off the disappointment quickly, attacking through Fortune, who clipped a nice ball to the near post where Carter nodded it onto the bar.
Time was always against them, however, and it wasn’t until the final two minutes that they fashioned another good chance, Maguire’s lovely through ball giving Carter a shooting opportunity that he slipped just wide.