A frustrated Steve Burr criticised his Blues said for failing to capitalise on an excellent chance to move away from the relegation mire against Welling United.
Wings midfielder Jake Gallagher was sent off on the half hour for a reckless tackle but his team-mates overcame the numerical disadvantage to ease to a 2-0 win.
Chester were sluggish and short on ideas, and the meek loss leaves the Blues teetering above the bottom four with five games to go.
Burr said: "It was a great opportunity, especially with Welling going down to 10 men, and we never took that opportunity or made that advantage count."
Second half goals exotically-named pair Vasilious Karagiannis and Ross Lafayette ensured the mid-table Wings won for the first time in six games.
Chester saw plenty of the ball but were unable to create any real scoring opportunities with home keeper Lee Butcher making only two saves - both routine catches.
Burr kept faith all but one of the side that recorded a 2-0 win over Tamworth with Jamie Menagh dropping to the bench as Gareth Seddon returned from illness.
But the manager said the players failed to repay the faith shown in them, with the second half performance as poor as any this season.
"We seem to take a few steps forward and then big steps backwards," said Burr.
"It was very disappointing."
Burr added three new faces to his squad at the tail end of last week but only one - Luke Ashworth - made the squad, but conceded the manner of the defeat left him wondering whether he had made the right call.
He said: "Maybe the reason behind that was the fact that I felt we did so well on Tuesday but then with a performance like that it makes you think that maybe you should have done
"We told the players the same. We should have taken advantage of Welling being down to 10 men
"They have got a reasonably good home record here and it was always going to be difficult.
"The pitch was difficult but it was the same for both teams and we won't get a better chance of three points than we had here."
Chester remain two places outside the relegation zone, but Aldershot Town and Dartford closed the gap with wins and have games in hand.
Burr said: "We are not in a good position at the moment. We didn't take advantage of them being down to 10 men and winning the game or doing enough to win the game so that was disappointing.
"There are still games and enough points to play for so we will keep going but we need a lot better if we are going to stay in this division."
Bottom club Hyde visit the Swansway Chester Stadium on Saturday (3pm) and Burr will know only three points will do.
Trips to play-off contenders Grimsby Town and Cambridge United look tough as do the final two home games against rivals Wrexham and well drilled Salisbury City.
Burr said: "I'm always hopeful because while there is still a chance you keep going don't you and you don't throw the towel in but we need to show a lot more than we did against Welling."
