Denbigh became the first team to beat Flint Town United at the Essity Stadium this season and advanced to the northern semi-final.
Silkmen manager Lee Fowler gave a number of the club’s youngsters a chance to shine, with 11 academy players either featuring from the start or on the bench.
Flint led early on through Luis Lacey, but Denbigh turned the game around to be ahead at half-time thanks to goals from Matthew Worrall and Ryan Kershaw.
Jean-Louis Akpa Akpro levelled the contest again just before the hour mark, but Josh Lock and Tom Weir earned the visitors a two-goal cushion soon after.
Harvey Drazdauskas’ first senior goal for Flint in stoppage time came too late in the day to save his side.
Jake Roberts’ penalty and Danny Warren’s composed finish came within four minutes of each other in the first half to put Mold in control, before Jamie Hyde struck a screamer to halve the deficit for Guilsfield just before half-time.
However, the hosts could not find an equaliser after the break. Alex striker Roberts was sent off for a second yellow card offence deep into stoppage time.
Revitalised Llandudno followed up three successive league wins by reaching the cup semi-finals at Victoria Park.
First half goals from Billy Nicholas and Harvey Bennett put the Seasiders in the ascendency, before Fabrizio Murtas added a third just after the hour mark.
Nyasha Mwamuka’s first goal for Llanidloes proved only to be a consolation.
Hosts Prestatyn progressed on penalties following a 1-1 draw in 90 minutes against Ruthin at Bastion Gardens.
Dan Atkins opened the scoring after just eight minutes, but the Seasiders had Kurtis Pearson and player-manager Karl Clair sent off on 62 and 88 respectively before substitute Andy Brown equalised for Ruthin in the 91st minute.
In the shootout, Owain Morris missed Ruthin’s second spot-kick and Prestatyn scored all of their first four before Ben Jones sent them through by netting from 12 yards.
Northern
Mold Alexandra v Denbigh Town
Prestatyn Town v Llandudno
Southern
Ammanford v Briton Ferry Llansawel
Llanelli Town v Cambrian & Clydach Vale
It is now six games without a win for Gresford after they went down 3-1 at home to Caersws in last Saturday’s only Cymru North fixture.
Craig Williams, Harry Cottam and Sam Phillips all netted for the Bluebirds, Toby Gallagher-Keenan with a consolation for the Colliers, whose Haci Ozlu missed a penalty just before the break with his side 2-1 down.
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