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Substitute Adrian Lopez struck deep into stoppage time to give Villarreal a precious advantage as they beat Liverpool 1-0 in an entertaining Europa League semi-final first leg at El Madrigal.
The striker had the simple task of tapping Denis Suarez's lay-off into an empty net after Kolo Toure had been caught out by a floated ball which the midfielder controlled superbly before breaking unopposed into the penalty area and squaring for Lopez to finish.
The outcome was rough on Jurgen Klopp's side who had given a good account of themselves over the 90 minutes, but slipped to their first loss in 12 European outings this season and must repeat the heroics of the previous round at Anfield if they are to make the final.
The Spanish side started brightly, but it was Liverpool who had the first chance of the game on four minutes as Joe Allen got on the end of Adam Lallana's low cross, but shot straight at Villarreal goalkeeper Andres Sergio Arsenjo.
The home side came close on 12 minutes with former Tottenham striker Roberto Soldado shooting narrowly wide after Liverpool's defence had failed to pick up his run into the penalty area to meet Bruno's quickly-taken free-kick.
Liverpool goalkeeper Simon Mignolet had to react quickly on 20 minutes to parry Tomas Pina's low drive before Lucas Leiva got across to block as the ball rebounded to the same player on the edge of the penalty area.
Villarreal continued to threaten and both Kolo Toure and Alberto Moreno made vital interceptions to snuff out dangerous balls into the Liverpool box.
Soldado was proving hugely influential in the Villarreal attack and was unlucky to see his snap shot from the edge of the area brush the outside of the post five minutes before the break as Mignolet scrambled across his goal.
But the Spanish side couldn't find a way through and Jurgen Klopp's side will have been pleased to have kept their hosts scoreless after an entertaining opening 45 minutes.
Villarreal threatened again immediately after the break, with Cedric Bakambu heading a Jonathan dos Santos corner against the outside of the post after midfielder Denis Suarez had carved open the Liverpool defence .
Mario then wastefully blazed over from a tight angle with a number of Villarreal players lurking inside the six-yard box.
But Liverpool were showing plenty of grit and determination and posed a significant threat themselves going forward.
Indeed, the home side were given a stark reminder of that threat on 65 minutes when Arsenjo just managed to get his fingertips to Roberto Firmino's low drive to turn the ball onto the post.
Liverpool looked more comfortable as the second half progressed and began to enjoy plenty of possession in midfield.
They appeared to have completely extinguished the Villarreal threat, but were almost behind five minutes from the end when Mignolet had to go full stretch to tip Bakambu's effort away for a corner after a through ball had completely opened up their defence.
However, they broke quickly from the resulting corner as Moreno's pace took him beyond the last man, but the full-back shot harmlessly wide with substitute Jordon Ibe well positioned in the middle.
Liverpool were made to pay in the cruellest fashion within a minute of Moreno's miss as, with the game now deep into stoppage time, the superb Suarez took advantage of a rare lapse from Toure to collect a floated cross-field ball before breaking into the penalty area and calmly squaring the ball for Lopez to score to give Villarreal a precious advantage heading to Anfield for the second leg next week.
By: Kieran O'Daly