Chester couldn't manage to overturn a third 2-0 disadvantage in the space of seven days - losing at Liberty Way to struggling Nuneaton.
An early goal from James Armson and a deflected free kick from Lee Fowler gave the hosts a comfortable half time lead. Substitute Craig Hobson pulled one back, but Marcel Barrington then scored to give the hosts breathing room once again. Hobson gave the Blues hope late on - but it proved to be mere consolation.
Steve Burr made one change from the excellent midweek win at Dartford, and it was enforced. Danny Harrison replaced the suspended Kingsley James.
The hosts almost took the lead in the seventh minute when Anton Brown's spectacular effort trickled inches wide of the post.
John Rooney then tested Boro's new loanee keeper, Christian Dibble, with a long range free kick which the keeper having to make a save - but Liam Daish's side took the lead moments later.
Michael Gash knocked the ball down and Armson was on hand to sweep the ball home from 12 yards. That advantage was doubled moments later when Fowler's free kick took a deflection hefty enough to wrong foot Jon Worsnop and find the net.
Rhys Oates has scored on the two previous occasions the Blues have gone two goals down this week, but he couldn't add another to his tally today. First, Dibble denied him with his body and then the Barnsley loanee striker could only hit the side netting after he'd rounded up his Tykes teammate.
Harrison and Gareth Roberts were replaced at the break by Ibou Touray and Hobson - and the latter of the subs made an instant impact when he glanced home from a cross from the right wing by Oates.
Hobson had the chance to level the match up in similar fashion just a minute later, but his header from Matty Hughes' cross was the wrong side of the post.
Adam Dawson was then twice denied by Jon Worsnop for Boro, who were looking nervy holding on to the lead.
Oates and Dibble was becoming the biggest duel of the match, as the keeper made the best save of the game to deny the forward after Hughes' backheel.
Nevertheless, the relegation strugglers hit Steve Burr's side with the sucker punch with ten minutes remaining.
Leicester loanee Dawson lead a charge forward for the hosts, and his low cross was tucked away by Barrington.
Hobson then reignited the fightback with two minutes of normal time remaining - nodding home from an excellent Sean McConville corner.
Rhys Oates then almost snatched an equaliser in added time, but - remarkably - he was denied yet again by Dibble from point blank rage to conclude yet another pulsating and entertaining Chester match.
Chester FC: Worsnop, Kay, Brown, Charnock, G Roberts (Touray 46), Rooney, Harrison (Hobson 46), Mahon, McConville, Hughes, Oates.
Subs Not Used: C Roberts, Peers, Menagh.
Goal: Armson 20, Fowler 23, Barrington 79; Hobson 50 & 88.
Referee: Paul Rees (Bristol)