Holders Chester FC will have to hand back the Cheshire Senior Cup trophy after Macclesfield Town progressed into the semi finals with a comfortable 2-0 win.
While the quarter final exit ends any hope of having silverware to parade come the end of the season, the Blues' struggles in the Skrill Premier mean there will be few lamenting the fact Steve Burr and his players can now concentrate on beating the drop.
Macc started first choice strikers Chris Holroyd and Scott Boden up front and that pair proved the difference between the side, bagging a goal each either side of the break.
Chester worked hard throughout and there were some positives, most notably the return to action of Nathan Turner after three months out and the encouraging performance of teenager Liam Blake.
Unsurprisingly given the importance of upcoming league games, Burr made nine changes from the 2-1 win over FC Halifax Town.
There was a welcome return for midfield workhorse Nathan Turner, out injured since the 2-2 draw with Hereford United on November 12.
Burr handed a rare start to back up keeper Martin Fearon and gave teenage duo Blake and Tom Peers a chance to impress.
Macc fielded a strong side with ex-Chester City striker Holroyd and the dangerous Boden leading the line and it was the visitors who shaded the opening quarter of an hour.
Boden beat the offside trap and poked past Fearon on five minutes but Paul Linwood recovered to clear with the ball trickling toward the goal line.
Jamie Menagh - the hero against Halifax - looked lively down the left for the Blues and Linwood then went close to opening the scoring but was unable to get his head to Craig Lindfield's curling free kick.
Holroyd wasted the clearest chance of the first half on 18 minutes, blazing over when clean through on goal with only Fearon to beat.
Macc keeper Richard Branagan then denied Lindfield from close range after a good ball from Jamie Reed but the Blues struggled to get past the visitors' commanding centre half Steve Williams.
Left winger Arthur Gnahoua came close for the Silkmen on 26 minutes but his deflected strike from the edge of the box hit the bar with Fearon beaten before Danny Rowe on the other flank dispossessed Linwood and drove into the box but Blake cleared behind.
Four minutes before the break, Macc took the lead when Holroyd pounced on a soft Ross Killock back pass and lifted the ball past Fearon before nudging into the net.
Blake went close to getting the Blues back on level terms second before half time but Branagan saved well down to his right as the visitors took a one-goal lead into the interval.
George Horan replaced Killock as the second half got began with the Blues skipper due to have an operation on his ankle next week, while Macc brought on Peter Winn for Danny Andrew.
Reed had half a chance to snaffle an equaliser when put clear but Branagan rushed out well to smother.
Macc went close when Gnahoua intercepted a sloppy pass and unleashed an angled shot but the woodwork denied him for the second time as his effort hit the bar and flew behind.
Compared to the opening 45 minutes, the second half was short on chances and quality with neither side able to settle.
As the game entered the latter stages the hosts began to turn the screw with frantic defending seeing Blake and Peers denied before Branagan made an excellent one-handed stop to keep out Peers' header after another fine Lindfield cross.
Blues youth team left back Tom Batten came on for his senior debut, replacing Lewis Turner for the final 15 minutes.
Blake, who showed some smart touches throughout, had a fine chance to equalise after a lobbed pass from Peers but the teenage midfielder got his header all wrong.
Burr threw on John Rooney for Nathan Turner, who got an important 80 minutes under his belt, for the final stages but the visitors sealed the win four minutes from time.
Winn swung over the ball from the left with four minutes to go and Boden sent his header over Fearon to put the Silkmen into the semi finals.
Chester FC: Fearon, Kay, Killock (Horan 45), Linwood, L Turner (Batten 75), Lindfield, N Turner (Rooney 80), Blake, Menagh, Reed, Peers.
Subs: Danby, Mahon.
Macclesfield Town: Branagan, Halls (Cowan 59), Williams, Pilkington, Andrew (Winn 45), Rowe, Turnbull, Lewis, Gnahoua, Holroyd (Bailey 59), Boden.
Subs: O'Keefe.
Goal: Holroyd 41, Boden 86.
Referee: John Dowd (Wirral)
Attendance: 415
