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:
1. Joel Dixon - 5
Still doesn’t quite demand his area to instil total confidence. Was a little fortunate when clattering into Colclough early in the second half and was rooted for the equaliser. Did make some decent stops, however, particularly from Jacobs and Colclough. Got something on the third but couldn't keep it out Booked for time wasting. Photo: FRANK REID 2022
2. Charlie Seaman - 5
As tough an afternoon as he is likely to have all season up against Colclough who got the better of him most of the game. Rarely saw him going forward as we have done due to being tested so much by Colclough. A little wayward in possession at times. Photo: FRANK REID NATIONALWORLD 2022
3. Kieran Wallace - 6
Looked a little lost as a third centre-back in the early stages but was much more comfortable when moved into midfield. Broke things up quite well at times in the first half and exchanged nicely with Cooke on occasion. Some decent blocks but tired in the second half and struggled to deal with wave after wave of Chesterfield attack. Subbed. Photo: FRANK REID
4. Emmanuel Onariase - 6
Real nervy start and some sloppy distribution but just about managed to deal with Grigg. Was forced into a lot of defensive work after the break. Some good clearances but couldn’t help keep Chesterfield out as set pieces continue to plague them. Will have easier afternoons. Picture by FRANK REID Photo: Frank Reid