Pools let a two-goal lead slip at the SMH Group Stadium as the Spireites struck deep into second half stoppage time to complete a remarkable turnaround.
Emmanuel Dieservwe gave Hartlepool the lead inside three minutes when racing clear of Ash Palmer to finish well before Anthony Mancini doubled the lead minutes later with a cool finish into the corner.
It was a dream start for John Askey’s side but they were soon pegged back as the impressive Ryan Colclough headed in to reduce the deficit.
Pools were dealt a significant blow when Mancini was forced off injured before Jamie Grimes levelled the scored early in the second half.
It was wave after wave of Chesterfield attack from that point on as Pools tried to hang on for a point.
But their resistance was broken five minutes into added time as Tom Naylor snatched a late winner.
And here is how Pools were rated:
5. Alex Lacey - 5
Moved over to the opposite centre-back role and found it challenging to deal with Colclough as well who dragged him out of position once or twice. Just wasn’t allowed to settle really which you credit Chesterfield for. Booked before being subbed. Photo: FRANK REID
6. David Ferguson - 5
Another who was pegged back in by Chesterfield for much of the game after an initial bright opening. Maybe a little fortune with penalty appeal against Naylor. One time he did find space in the second half he wasted a decent crossing position. Photo: FRANK REID
7. Tom Crawford - 5
Went close with a header in the first half and generally helped in Hartlepool’s excellent start. Took a heavy challenge from Mandeville which he had to recover from before being swamped in the second half. Booked. Photo: FRANK REID
8. Callum Cooke - 6
Started well and looked lively. Contributed to the opening goal and looked capable of breaking the lines. Some decent exchanges in midfield. Tasked with much more defensive work in the second half. One decent driving run after the break but a little wasteful with the effort. Photo: FRANK REID