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).
Source: BBC