The Spireites were sunk by a skidding 17th-minute shot by Nicky Featherstone and the bright start to the season from Martin Allen’s side – three straight wins and clean sheets – now seems a distant memory.
Martin Allen had described his team’s display against former club Barnet on Saturday as “very disappointing, bland, average and boring” and at the Super 6 Stadium they did not fare any better fading badly after a bright start.
The Spireites boss made four changes at the Vic, bringing in Haydn Hollis at the back for his debut in a 3-5-2 formation, while introducing Joe Rowley into midfield, Sam Muggleton down the left and Gozie Ugwu up top, where he partnered Zavon Hines.
Muggleton, playing at the ground where dad Carl plied his trade three decades ago, was the busiest man in an orange jersey.
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The 22-year-old was tasked with firing in his Exocet missile of a long throw and it gave the home side some uncomfortable moments.
But it was along the floor where the visitors almost got in on 15 minutes when Rowley was denied in the box by a sliding Featherstone tackle.
Having saved his side in one box, Featherstone made his presence felt in the other area two minutes later, firing a left-footed grass-cutter into Callum Burton’s left corner after a fine home move.
It was the cue for Hartlepool to come forward at will and Michael Woods and Mark Kitching both missed golden opportunities.
Will Evans was having an uncomfortable afternoon at the back and Allen made a change on 33 minutes, withdrawing the defender and bringing on Kyel Reid and switching to a 4-4-2 system.
It transformed the Spireites instantly and Hines should have levelled in the 37th minute after a Muggleton long throw, only to hit his shot at Scott Loach, while soon after the Pools keeper made a fine save to keep out a deflected Muggleton strike.
After the break, Hollis fired high over bar after a Chesterfield corner but, despite the introduction of Marc Antoine Fortune, the Spireites were only able to huff and puff.
Sub Kyel Reid did force Loach into a fine save and had an injury-time attempt blocked but, otherwise, there was little danger to the home goal.