Gillingham 1 Chesterfield 1: Anderson saves point for Spireites at the death
The struggling Spireites have picked up only two points in the four games since Caldwell - who won Wigan Athletic the league last season - took over.
The visitors have failed to find the back of the net with any sort of regularity away from home this season, and the same issue arose at Priestfield.
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Hide AdAnderson was the hero as his stoppage-time equaliser cancelled out Max Ehmer’s header.
The battling point leaves the Spireites six points from safety, with a real job on their hands to avoid relegation.
The Gills had the majority of the clear-cut chances. Star striker Ched Evans missed the trip through injury as teenage Queens Park Rangers loanee Osman Kakay made his debut.
Goalkeeper Lloyd Allinson had mor work to do than opposite number Stuart Nelson.
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Hide AdThe struggling Spireites almost went behind after just five minutes. Jay Emmanuel-Thomas directed Rory Donnelly’s header towards goal, with Caldwell’s men scrambling the ball off the line.
Emmanuel-Thomas then fired a volley wide of the target, before Reece Mitchellfired wide at the other end.
Anderson rose highest to head over from a corner before the Gills should have scored. Donnelly pulled the ball back for Cody McDonald, who took too long to pull the trigger as his strike was deflected into the arms of Allinson.
Donnelly was a constant thorn in the Spireites’ side, and the best chance fell to the Northern Irishman as he rattled the inside of the post on the half hour mark.
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Hide AdJon Nolan limped off late in the half to give Caldwell another injury headache.
The Spireites had to do just as much defending after the interval. Minutes after the restart Evatt did well to divert a cross away from the danger area, with McDonald waiting to stroke home inside the box.
Eleven minutes into the second period Allinson had to be alert to parry McDonald’s effort away from danger.
On the hour the visitors were let off as Scott Wagstaff failed to get on the end of Emmanuel-Thomas’ dangerous ball. Rai Simons forced Nelson into a sublime stop after going through on goal. But the visitors were made to rue that miss as Ehmer headed home Ryan Jackson’s long throw.
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Hide AdAnd two minutes later as the defence had to clear McDonald’s backheel off the line.
Debutant Kakaywent close late on as Nelson pulled off a stunning stop.
With virtually the last touch of the game Anderson slotted home the rebound from Evatt’s effort.
gillingham: Nelson, Jackson, Ehmer, Oshilaja, Garmston, Wagstaff, Wright, Dack (Martin, 90+2), Donnelly, Emmanuel-Thomas (Byrne, 89), MacDonald (Parker, 84).
Unused subs: Holy, List, Hessenthaler, Osadebe.
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Hide AdCHESTERFIELD: Allinson, Anderson, Evatt, Donohue, Kakay, Nolan (Martinez, 45+4), Gardner (Ebanks-Blake, 72), Grimshaw, Mitchell, Dennis (Simons, 64), Faupala.
Unused subs: Duke, El-Fitouri, Hird, Brown.