Arsenal were knocked out of the Europa League at the last-16 stage in a penalty shootout rout by Sporting Lisbon at Emirates Stadium.
Gabriel Martinelli's spot-kick was saved by goalkeeper Adan before Nuno Santos got the winner to ignite celebrations among sporting's players at full-time following a momentous and entertaining tie.
A hair-raising long-range chip by Pedro Goncalves from 46 yards constrained additional time after Arsenal Granit Xhaka had before jumped on a rebound for the opener.
Arsenal defender Gabriel came excruciatingly close twice in the last minutes of additional time when his header was tipped over the bar, and afterward he had a work cleaned up the goalline.
Sporting's Manuel Ugarte was likewise shipped off after a dangerous sliding tackle on Bukayo Saka minutes before their shootout victory.
There were chances all through in this frantic second leg as Arsenal substitute Leandro Trossard hit the post in additional time when he was gifted belonging and went through one-on-one with the goalkeeper, just for Adan to touch it onto the woodwork.
Sporting forward Marcus Edwards, previously at Tottenham, was likewise denied by goalkeeper Aaron Ramsdale minutes after Goncalves made it 1-1 in normal time.
The guests will figure out their quarter-final opponents in Friday's draw (11:00 GMT).