Villarreal scored a 92nd-minute winner to gain a 1-0 first-leg lead in their Europa League semi-final against Liverpool this evening.
Both sides struck the woodwork in a largely cagey affair at El Madrigal, but Adrian Lopez netted an injury-time winner to hand the Spanish outfit a slender lead heading into next week's second leg at Anfield.
The visitors created the first big chance of the match after just five minutes when Adam Lallana's low cross into the middle deflected into the path of Joe Allen, but the midfielder fired his effort straight at the keeper when he should have done better.
Villarreal responded with a chance of their own shortly afterwards when Bruno Soriano's quick free kick over the top found Roberto Soldado in the area, but he sent his half-volley bouncing narrowly past the far post.
The match was developing into an even contest as both sides enjoyed spells in the ascendancy, but neither goalkeeper was particularly overworked, with Liverpool only managing further long-range efforts from Lucas Leiva, Lallana and Philippe Coutinho before half time.
The hosts did have more joy in the final third, and almost took the lead midway through the half when Jonathan dos Santos knocked the ball back to Tomas Pina, whose low curling effort was pushed away by Simon Mignolet.
Marcelino's side came close again shortly before half time when Bruno fed a pass in to Soldado, who turned and curled an effort narrowly wide from 25 yards.
Villarreal came flying out of the blocks for the second half, winning a corner in the first minute from which Cedric Bakambu glanced a header against the outside of the post.
Liverpool hit the woodwork themselves shortly after the hour mark when James Milner's clever pass found Roberto Firmino inside the box, and the Brazilian's spin and shot was turned against the foot of the near post by a smart Sergio Asenjo stop.
The bulk of the second-half action was confined to the final few minutes, however, and it was sparked by a rare moment of space for Bakambu as the dangerous striker got in behind Liverpool's defence for the first time, only to be thwarted by a full-stretch save from Mignolet.
Liverpool broke from the resulting corner after Denis Suarez had fluffed his lines to allow Alberto Moreno to race clean through on goal, but the Villarreal midfielder recovered enough to put pressure on Moreno, who lashed his shot off target.
Suarez was to prove vital when the winner came too as he collected a long pass over the top to find himself with only Mignolet to beat, before unselfishly squaring the ball to give Lopez the simplest of finishes.
The result sees Liverpool lose in the Europa League for the first time this season, while Villarreal, who have won all seven of their home matches in the competition, equal Liverpool's record of 12 Europa League games unbeaten in a single campaign.
