Villarreal, the proverbial European semi-final bridesmaids, are on course to reach their first ever showpiece occasion after holding Liverpool to a 1-0 win in their Europa League first leg at Estadio El Madrigal.
Having lost at this stage three times in two competitions before, boss Marcelino Garcia Toral held hopes of making history against a team looking to reach their second final this season, and Adrian Lopez’s late strike gives them the advantage.
The tone for the game was set early on, with space in the midfield and both sides’ propensity to counter attack at pace leading to an end-to-end encounter, but few first half opportunities.
It was Liverpool who had the first, and best, chance of the half just five minutes in, but Joe Allen could only shoot tamely at Sergio Asenjo in the Villarreal goal.
Bruno, the host’s captain, was a bright spark in the early stages, pulling the strings from the centre of the pitch.
Goalmouth action was at a premium, though, despite Denis Suarez and Mario Gaspar looing lively out wide, with the Liverpool defence keeping 22-goal striker Cedric Bakambu quiet for large spells.
Jurgen Klopp’s side, fresh from knocking his former club Borussia Dortmund out in spectacular fashion, were largely restricted to shots from distance, clearly lacking the attacking penetration of the injured Divock Origi and Daniel Sturridge, who was on the bench.
It wasn’t until the 41st minute when Villarreal went close again, Bruno again playing a lovely through ball into Roberto Soldado, who could only shoot wide on the turn.
The Premier League outfit showed their experience in European competition, keeping it tight in midfield, continuing to restrict Villarreal, while beginning to probe themselves as the game went on.
Roberto Firmino, who had struggled throughout in the lone striker role, sprung into life on 65 minutes, hitting the post with a well struck shot after linking up well with James Milner, Asenjo getting a slight touch to keep him at bay.
The continued absence of Sturridge told the story, and Klopp seemed more than happy to avoid defeat ahead of the return leg at Anfield next Thursday.
But it went terribly wrong for the German when Lopez struck, tapping into an empty net after a break away.
The complexion of the tie completely changed with Villareal’s late goal, but Liverpool will remain confident they can turn things around once again at Anfield.