HARTLEPOOL United, who Burton Albion play on Saturday, fell to their fifth defeat in succession as Chesterfield left Victoria Park with all three points.
The Brewers' play-off rivals pressed from the kick off, giving goalkeeper Andy Rafferty plenty to do in the opening minutes of his first home start of the season.
Pools were left to look to the counter, with Luke James once again showing a great workrate and doing plenty of running in the final third.
Darren Holden got in a crucial block as the lively the influential Sam Morsy set up another attack for the visitors, and Jack Barmby arrived to hook clear the resulting corner.
Simon Walton was looking solid for Pools and put in a few important challenges to stop the Chesterfield attack as the powerful midfielder denied both Sam Hird and Marc Richards with impressive blocks.
Pools’ first chance on goal arrived on 19 minutes as Brad Walker set up Jack Compton for a shot on goal, but the winger sent his effort high over the bar.
At the other end, full debutant Scott Harrison got in a great block to deny Morsy inside the box, while Andy Rafferty remained strong – dominating his area, particularly in the air.
With 24 minutes on the clock Pools took the lead slightly against the run of play. Jack Barmby slipped a well-timed ball through for Luke James and the young striker showed great composure as he took the ball forward to shoot past Tommy Lee and into the bottom left corner of the net.
Chesterfield were level within six minutes as they capitalised on a succession of corners - a ball in from the left created a scramble inside the box and Liam Cooper was allowed the room to poke home from close range.
Pools had a half chance before the break to re-take the lead when Sam Collins met a corner to send a header at goal but the skipper’s effort was cleared off the line.
It took Chesterfield less than five minutes of the second half to take the lead as they once again burst into action.
Eoin Doyle hit a spectacular effort from the right side of the area which beat Rafferty to sneak in at the far post to make it 2-1.
Doyle went desperately close to making it 3-1 on the hour mark when he picked up the ball from the lively Gary Roberts but he sent his effort wide after looking set to score.
With 65 minutes on the clock, manager Colin Cooper had made changes in a bid to give his side that lift – with James Poole and Jonathan Franks both coming on.
And Pools did start to see a bit more of the ball, mostly down the left hand side and it was still James who offered the main outlet for his side going forward.
Despite often finding himself with little in the way of support, James continued to plug away and proved a real handful for the visiting defence.
Scott Harrison did have a strike on goal from the edge of the area but his effort was blocked by a blue and white shirt and
At the other end, Rafferty pulled off a great save to deny sub Armand Gnanduillet, who looked set to make it 3-1 with an effort from close range.
James was pulled down just to the right of the box winning a freekick for his side but, despite a good delivery from Walton, the opportunity passed for Pools.
Pools threw everything forward in the closing minutes of the game, with Collins joining Marlon Harewood up front as the side looked for a late equaliser, but there was no way back into this game for Cooper's side.
POOLS: Rafferty, Duckworth, Collins, Harrison, Holden, Walton, Walker (Oliver 80), Compton (Franks 62), Barmby (Poole 60), James, Harewood; subs not used: Flinders, Hawkins, Richards, Jones.
CHESTERFIELD: Lee, Hird, Evatt, Morsy, Cooper, Darikwa, Smith, Kearns (Humphreys 60), Gardner (Roberts 57), Doyle, Richards (Gnanduillet 80); subs not used: Dunbavin, Togwell, O’Shea, Beesley.