Arsenal were knocked out of the Europa League at the last-16 stage in a penalty shootout defeat by Sporting Lisbon at Emirates Stadium.
Gabriel Martinelli’s spot-kick was saved by goalkeeper Adan before Nuno Santos netted the winner to spark celebrations among Sporting’s players at full-time following an eventful and entertaining tie.
A sensational long-range chip by Pedro Goncalves from 46 yards forced extra time after Arsenal’s Granit Xhaka had earlier pounced on a rebound for the opener.
Arsenal defender Gabriel came agonisingly close twice in the final minutes of extra time when his header was tipped over the bar, and then he had an effort cleared off the goalline.
Sporting’s Manuel Ugarte was also sent off after a dangerous sliding tackle on Bukayo Saka minutes before their shootout victory.
There were chances throughout in this frenetic second leg as Arsenal substitute Leandro Trossard hit the post in extra time when he was gifted possession and ran through one-on-one with the goalkeeper, only for Adan to touch it onto the woodwork.
Sporting forward Marcus Edwards, previously at Tottenham, was also denied by goalkeeper Aaron Ramsdale minutes after Goncalves made it 1-1 in normal time.
The visitors will find out their quarter-final opponents in Friday’s draw (11:00 GMT).
Despite the score being 2-2 on aggregate going into the match, Mikel Arteta made five changes to the Arsenal starting XI as he tried to make full use of his squad in the midst of a Premier League title race.
There was a welcome return for striker Gabriel Jesus, making a first start since December after recovering from a knee injury, but he could not convert before going off at half-time.
And Arteta was dealt an early blow when injuries to defenders William Saliba and Takehiro Tomiyasu forced him into first-half substitutions.
Sporting began well, controlling possession and creating numerous opportunities, despite Xhaka’s powerful strike giving Arsenal a narrow lead.
They had a flurry of chances immediately after Goncalves’ stunning equaliser too – Paulinho flicking a header over the bar and Edwards being denied by Ramsdale.
England goalkeeper Ramsdale had a busy evening, while Trossard, Martinelli and Gabriel all tested Adan at the other end.
Arsenal’s European journey comes to an end but Arteta’s concern will be the impact it could have on their Premier League campaign.
Injuries to key defenders and 120 minutes of gruelling action is not ideal preparation for their next league game against Crystal Palace in three days’ time.
Arsenal goalkeeper Ramsdale was in the thick of the action but ultimately could not have a say in the penalty shootout.
Goncalves’ audacious chip from just over the halfway line in normal time saw Ramsdale scrambling back to his goal in a helpless attempt to prevent it going in.
The equaliser stunned Arsenal and they were pinned back for minutes afterwards before Ramsdale responded with a superb save to deny Edwards when he raced through on goal.
As extra time kicked in, it felt inevitable Ramsdale would be called into action again in a shootout and he almost made his mark, getting his fingertips to Gonçalo Inacio’s spot-kick, only to see it nestle inside the post as a wry smile crossed Ramsdale’s face.
Defeat ends a run of six matches unbeaten in all competitions for Arsenal.
