Last season’s NWCFA Junior Challenge Cup finalists, Mountain Rangers and Llandyrnog United, will meet in the 2026-27 quarter-finals.
Both sides advanced to the last eight on Saturday to set up a repeat of last term’s showpiece, which Rangers won 2-1.
Holders Rangers edged through to the last eight – but victory at Pentraeth came at a cost.
Despite saving a penalty in a shoot-out to ensure the Caernarfon area side advanced, keeper Dylan Roberts sustained a broken ankle during the game which will confine him to a spell on the sidelines.
Rangers started the brighter, but Pentraeth took a sixth-minute lead when an ambitious effort from Tom Jones just inside the away half sailed in over the goalkeeper.
The visitors responded by pushing hard for an equaliser, and their pressure paid off when Dylan Owen picked out an unmarked Aeron Williams, who made no mistake to bring the scores level going into half-time.
Rangers came out strongly after the break, with Aeron Williams having two further efforts ruled out for offside and handball. Pentraeth then struck to make it 2–1, Marquis Holland on target with a cracking header, leaving the holders with work to do.
With the clock ticking into stoppage time, Cai Owen fed a lovely ball into substitute Dion Jones, who levelled it at 2-2 to send the tie to penalties.
The shootout delivered even more drama, with Rangers showing nerves of steel to score all six of their penalties, while Dylan Roberts produced a crucial save to help send the holders through.
Jordan Pritchard and Luke Gardiner delivered the goals which earned Rovers an away quarter-final against either Rhuddlan Town or Blue Bridge.
Sub Jamie Williams pulled one back for Cernyw, but it was not enough.
Shaun Davies grabbed the 69th minute goal which qualified Henllan for the quarters where they will host Llanerchymedd.
Both sides had a player sent off – Elgan Hughes saw red for Henllan on 53, while James Jones received a second yellow for Caergybi on 88.
After the heartbreak of their last-gasp FAW Amateur Trophy exit at Conwy Borough the previous weekend, Llysfaen bounced back brilliantly to reach the Junior Cup last eight.
Jordan Russell and Steven Collins both scored in the opening 18 minutes for the visitors and that was sufficient to see them through, Crozzy unable to respond until 87 via Josh Baxter.
A remarkable Anglesey derby saw Llanfairpwll squeeze through by the odd goal in 11.
Hat-trick hero Ashley Davies produced an 86th minute decider for the home team.
Cefni led 4-2 at one stage early in the second half, only for Pwll to roar back to lead.
Home scorers were: Ashley Davies 3, Aled Davies, Jake Turnbull (2, 1 pen).
Replying for Cefni: Dion Owen, Will Edwards, Lewis Owen, Aaron Jones, James Lewis.
Llandyrnog made it 10 straight wins in all competitions this season with a hard-earned success at fellow North Wales Coast East Division One outfit Meliden.
Josh Griffiths and Alex Webster bagged the first half goals which won the day for Dyrny.
Llanerchymedd recovered from 2-1 down at half time to seal a quarter-final match at Henllan.
Kelvin Berks struck twice in the first half for Athletic, Jay Jones replying with Jamie Patterson also missing a penalty for the visitors.
Eight minutes into the second half, Josh Evans made it 2-2, then Patterson netted on 76 and 83 minutes to seal the tie.
Rhuddlan Town or Blue Bridge v Bethesda Rovers
Llanfairpwll v Llysfaen
CPD Mountain Rangers v Llandyrnog United
CPD Henllan v CPD Llanerchymedd
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