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 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.