Playing their illustrious opponents for the first time at a windy Childwall in Liverpool, the hosts fell behind when Aron Goldman bundled the ball over the line from close range a minute before the interval.
Haroldeans equalised on 55 minutes when Paul Harris curled an exquisite free-kick into the top corner from 25 yards.
With no further goals, the match went into extra-time, which featured two 10-minute spells. Defences dominated during this period in a tie where there were three cautions for both teams.
The teams could not be separated so it went to penalties to see which team would join Maccabi London Lions, HMH and Mill Hill Dons in the semi-finals.
Both teams struck the post with their first efforts before Eden Harris showed an ice-cool temperament to put Haroldeans ahead. Then 17-year-old Clein came to the fore, saving two Maccabi spot-kicks. Maxim Green also converted in a tense shoot-out as Haroldeans progressed 2-1.
Haroldeans’ chairman Fraser Saville told JC Sport: “We’ve beaten one of the best teams in Jewish football and have consistently shown we can compete with any team in the competition.
“We’ve never played Manchester 1st before so this shows how far we have come.”
Looking ahead to tonight’s draw, Saville added: “I think this win will make the London teams stand up and fear us.”
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