It was the visitors' first win in 13 matches - unlucky for a Stags side that have now lost a new club record seven straight games at Field Mill and were booed off the field at the end.
- Billy Dearden reaction, including audio interview
Earlier in the day boss Billy Dearden even went to the extent of taking his squad for a pre-match meal and get-together as they do for away games of which they have impressively won their last five. But the ploy failed to work.
John Mullins had even put them in the driving seat in the last minute of the first half with a great header.
But Kevin Ellison was allowed a free header for the equaliser.
Stags were then down to 10 men with star defender John Mullins off for a cut head when the visitors were given a penalty which they netted and Ellison put the icing on the cake in stoppage time at the end with Chester's third.
Stags felt they might have had a couple of penalties and Paul Linwood made a goal line clearance as nothing went for them in a disastrous second half.
It was the first of three 'six-pointers' against relegation rivals in eight crucial days for the Stags and the worst possible start they could have made to them.
Victory over Bury on Tuesday at Field Mill now is of paramount importance.
Mansfield made the one enforced change with Lee Bell out injured, D'Laryea coming into the centre of midfield.
The visitors were boosted when both Ellison and Wilson were declared fit after struggling all week with injuries.
From the kick-off Briggs launched the ball into the danger zone and Chester somehow survived five attempts at goal in succession.
Keeper Danby was down to block D'Laryea's low shot but the ball ran loose and Louis, Boulding and Atkinson all failed to turn it home before Dawson finally blazed over.
Stags continued to dominate the early stages though went to sleep on 12 minutes when Dinning's through ball almost found an unmarked Hughes in the box, but he was stretching too much to be able to guide it on target.
There was another scare for Stags when Roberts cleverly flicked the ball over Mullins to get sight of goal but curled his finish wide of the far post.
Dinning was well wide with a hopeful 20 yard volley from a clearance on 18 minutes as the visitors seemed to be emerging from their early shells.
Jelleyman did well to get in ahead of Partridge in the box as he tried to get on the end of Ellison's long cross. Then Vaughan curled one wide from 35 yards.
City forced two successive corners in what was becoming an increasingly scrappy affair.
The sides swapped further flag kicks. Then Butler twice produced good pieces of defending to deny Boulding.
The first time Boulding beat Danby to a through ball on the edge of the box and flicked it over him, but Butler was there to tidy up before the Stags striker could reach the ball.
Then he got in a good block on Boulding at the near post as he swung a leg at a Hamshaw cross.
Soon after Louis was unable to turn on at Atkinson cross but the ball bounced to Hamshaw whose overhead effort was straight at Danby.
A great tackle from Atkinson set up another Stags attack and Dawson's cutting through ball saw Hamshaw miscue at the vital moment. But this was much brighter from the home side.
And they dramatically grabbed the lead in the final minute of the half from another corner. Hamshaw sent it in from the right and Mullins rose unchallenged to power home a decisive header.
Chester sent on Holroyd for Butler for the second half.
Mansfield were first to threaten as Boulding's cross was just too high for Louis in space on the far post.
Louis did well to put Hamshaw in space on the right and he whipped in a hard, low cross in front of goal which Louis just couldn't quite reach.
Stags then broke well after clearing a corner with Hamshaw leading the charge. He could have sent Boulding away but delayed and then tried to put Atkinson in only to see the youngster's first touch bounce into touch.
However, from out of the blue City were level on 57 minutes. Partridge crossed from the left and Ellison stole a march on the defenders to head powerfully home.
Dawson was too high from 25 yards on the hour and then Linwood headed off the line after Dawson's low cross took a deflection from a well-worked free kick.
Hughes was booked for a tackle from behind on Boulding on 69 minutes and another training ground free kick routine cued up Briggs who sliced wide from 25 yards.
But, with the home side down to 10 men with Mullins off the field receiving treatment for a facial injury, Stags suddenly found themselves behind from the penalty spot,
Chester took advantage of the depleted defence as a clumsy challenge from striker Louis on Linwood as he turned saw the referee point to the spot and Dinning was cool as a cucumber to stroke the ball home with Muggleton going the wrong way.
Murphy had the ball in the Stags net again three minutes later as he nodded home a Vaughan free kick but, to Mansfield's relief, he was penalised for pushing.
Hughes should have settled the game on 77 minutes as he fired over from eight yards from a Partridge cross.
Buxton was cautioned for hauling back Holroyd as he tried to get away from him 11 minutes from time.
Boulding's luck was out on 81 minutes when he swivelled to get in a looping header from Dawson's cross but watched it land on the roof of the net.
Stags sacrificed Jelleyman at the back to throw Brown on as an extra forward.
But it was Muggleton who had a save to make as he kept out Murphy's header from a Partridge cross.
Louis was over the bar with a hopeful 25 yard strike as time began to run out on the increasingly desperate home side.
Louis was also well wide on the turn after being fouled and then Brown failed to get a head on Briggs' cross.
On 89 minutes Stags were denied what looked a clear penalty when Roberts caught Dawson in the box and the Irishman went down. But the referee waved play on as he had when Hamshaw had gone down in the box earlier.
Sorry Stags were finally killed off when City caught them pushing forward in stoppage time and Ellison sealed the points with a classy finish on the turn, curling the ball across Muggleton and inside the far post.
MANSFIELD: Muggleton, Mullins, Jelleyman (Brown 81), D'Laryea, Hamshaw, Dawson, M. Boulding, Buxton, Louis, Atkinson, Briggs. Subs not used: White, McAliskey, Holmes, Wood.
CHESTER: Danby, Dinning, Butler (Holroyd ht), Partridge, Murphy, Ellison, Hughes, Wilson, Linwood, J. Vaughan, Roberts. Subs not used: Palethorpe, Sandwith, Grant, S. Vaughan.
REFEREE: David Foster of Tyne and Wear.
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