A fortnight after an added-time winner put Liverpool into the last four of the Europa League, a similar fate befell them as they lost their semi-final first leg 1-0 in Villarreal.
The match appeared to be heading for a stalemate until substitute Adrian Lopez poked home two minutes into injury time.
Elsewhere, Kevin Gameiro’s late penalty gives Sevilla “life” in their Europa League semi-final against Shakhtar Donetsk, according to fellow goalscorer Vitolo.
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Liverpool went closest in the first half when Roberto Firmino hit the post.
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But Adrian Lopez tapped in to secure a dramatic late winner for Villarreal.
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The Europa League semi stays delicately poised ahead of the return leg at Anfield.
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Liverpool are hoping to reach a first European final in almost a decade.
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Vitolo's goal gave Sevilla an early advantage against Shakhtar Donetsk.
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But the hosts rallied through Marlos and Taras Stepanenko to go 2-1 up.
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However Kevin Gameiro's penalty ensured his team left with a draw & two away goals.
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Sevilla stayed on course for a third straight Europa League title.
