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:
13. Brody Paterson - 6
Brought on to try and help Ferguson but was booked within minutes of his introduction. Did get forward once or twice late on as Pools half threatened to pinch the game. Photo: FRANK REID NATIONALWORLD 2022
14. Jake Hastie - 6
One decent run late on to beat his man before standing a cross up to Ferguson. Couldn’t help Pools get out, however. Picture by FRANK REID Photo: Frank Reid