Tom Naylor scored the winner in the 95th minute to complete a remarkable comeback in front of a stunned but jubilant home crowd.
The Pools, who had won all of their previous four games and topped the table, led 2-0 after just six minutes through former Spireite Mani Dieseruvwe and Anthony Mancini.
But Ryan Colclough headed one back on 14 minutes and Jamie Grimes nodded in an equaliser one minute after the break.
And the Spireites won it five minutes into seven added-on when Naylor finished from inside the box to send the Town fans bonkers.
After an awful start, Chesterfield had recovered well and been the better side after the two early goals and deserved to win, with the Pools pinned back and clinging on.
The wait for a clean sheet goes on, but the Blues are pure box office for entertainment.
Chesterfield would have wanted to bounce back after Saturday’s defeat to Altrincham but they got off to a disastrous start, conceding twice in the first six minutes.
First, Ash Palmer got outmuscled on the ball by Dieseruvwe and he drove forward and slotted in after just two minutes.
And four minutes later the Pools doubled the lead after more poor defending from the home side, who were cut open like a knife through butter before Mancini was given far too much time and space to slide the ball in.
It could have got really embarrassing had Tom Crawford’s glancing header from David Ferguson’s inswinging free-kick gone in instead of landing on the roof of the net.
But Town were the better team for the rest of the half and should have been level by the break.
Will Grigg found himself one-on-one but a heavy touch took the ball away from him and ran through to goalkeeper Joel Dixon.
The Blues started to cut through the visitors and they pulled a goal back when Mandeville’s clipped cross from the right was headed in by Colclough for his third goal of the season and Mandeville’s fourth assist already.
The Pools were dealt a big blow when the impressive Mancini was forced off with a hamstring injury on 20 minutes.
Chesterfield’s dangerous attacks kept on coming as Colclough hit the side-netting and Jeff King curled over after a sweeping move.
Both sides continued to trade blows like a heavyweight boxing match, and this time it was the Spireites who were let off the hook after Dieseruvwe went through on goal but he was controversially denied by the offside flag. It was a decision that left Paul Cook with a smile on his face and his opposite number John Askey with his hands on his head.
Town should have equalised before half-time when, similar to their first goal, Mandeville clipped in a cross but this time Michael Jacobs headed straight at Dixon when really he should have scored.
But Chesterfield were level just one minute into the second-half when Naylor headed Mandeville’s corner onto the bar and Grimes nodded in the rebound.
Hartlepool were now on the ropes and the Spireites looked to have a strong shout for a penalty when Naylor appeared to be clipped in the box but referee Garreth Rhodes was unmoved.
On 60 minutes, the whole ground stood and applauded well-known Spireites fan Tony Brooks, who sadly passed away recently.
Soon after, the blistering Colclough rippled the side-netting with a low drive after bursting into the area.
With 20 minutes remaining, man of the match Colclough thought he had put Chesterfield in front from close-range but the offside flag was up.
Armando Dobra came on with 15 minutes to go and he almost had an immediate impact, creating a brilliant chance for Colclough, whose first-time shot went narrowly past the post.
Chesterfield continued to be on the front-foot in the latter stages and substitute James Berry, who was very bright, was denied a goal by a last-ditch block.
With the clock ticking down, Berry then stood up an inviting cross but Grigg headed wide from about six yards out which left Cook with his hands on his head.
But his hands were in the air in jubilation when Naylor pounced in the fifth minute of seven added-on to complete a remarkable turnaround and spark amazing scenes.
Chesterfield: 4-2-3-1: Tyrer; King, Palmer, Grimes, Horton; Jones (Oldaker, 83), Naylor; Colclough (Berry, 80), Mandeville, Jacobs (Dobra, 78); Grigg.
Unused subs: Williams, Quigley.