Midfield battler Tony Sweeney returned from a three-game ban to grab a match-winning hat-trick.
The 21 year old had given Hartlepool what should have been a match-winning lead before the game was ten minutes old, but he was needed to grab a late winner after Chesterfield staged a brave recovery either side of half time.
Hartlepool got off to a tremendous start as Sweeney took hold of the game by the scruff of the neck.
His first, with three minutes gone, was a close-range finish after great work by Adam Boyd on the right.
The second was a powerful shot from the edge of the area after Eifion Williams made the chance on the left.
Chesterfield were struggling to stay in the game as Hartlepool's pace tore them apart.
But the visitors got a surprise lifeline on 25 minutes when home keeper Jim Provett was judged to have fouled Wayne Allison, though it looked more of a stumble by the Chesterfield striker.
Provett was booked and Shane Nicholson slotted his third penalty of the season.
That put the wind up Hartlepool as the home team lost their way and Chesterfield came back well to take control without making it count before the break.
But after half time they did the trick. Steve Blatherwick had a goal disallowed just after the break for a foul as he headed in a corner.
But they were level on 50 minutes when Allison headed down a cross and Mark Stallard forced the ball in from close range.
It was anybody's game now, but it was Pool's turn to fight back, and they just about deserved their late winner.
It came on 83 minutes when teenage substitute Steve Turnbull blasted in a low shot which Carl Muggleton couldn't hold and Sweeney pounced to score from close-range.