Linfield are out of the Europa League on away goals after a heartbreaking 2-1 defeat by FC Xanthi at Windsor Park.
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The Irish Premiership side had led 1-0 from the first leg but Pereira Marcelinho's goal in the 27th minute levelled the game on aggregate.
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The Greek side had Konstantinos Fliskas sent-off just before half-time.
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Michael Gault scored a superb volley in the ninth minute of extra-time but Marcelinho squeezed in a shot at the near post to put Xanthi through.
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They now face Belgian side Standard Liege in the third qualifying round.
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Linfield can be proud of their display but will be desperately disappointed having come so close to a memorable triumph.
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Blues boss David Jeffrey had warned about the threat of the Greek side and the Irish league side suffered a setback when Marcelinho worked his way in from the left wing to net a low shot from an acute angle.
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Linfield's best chance came when Peter Thompson headed inches wide from Matthew Clarke's fine delivery.
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Fliskas was red-carded just before the interval for a bad tackle on Michael Carvill but there were no goals in the second half so the tie went to extra-time with the teams locked on 1-1 on aggregate.
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The pendulum swung Linfield's way when skipper Gault crashed in a fantastic volley to put the Belfast club 2-1 up overall, 1-1 on the night.
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But dreams of a third-round meeting with Standard Liege were ended when Marcelinho's shot beat Blues keeper Jonathan Tuffey at his near post.
The Europa League is still a competition every clubside would like to move into.....No matter how much of a 'losers competition' it is.