Sporting Lisbon goalkeeper Antonio Adan saved a penalty from Arsenal’s Gabriel Martinelli to secure a 5-3 shootout victory for the Portuguese side following a 1-1 draw in their round of 16 Europa League clash on Thursday.
The teams finished level at 3-3 on aggregate in the tie but the Lisbon club, fourth in the Portuguese league standings, advanced to the quarter-finals after Adan kept out Martinelli’s weak effort.
Premier League leaders Arsenal went ahead when a brilliant ball from Jorginho set Martinelli away on the left and after his shot was saved, Granit Xhaka followed up to smash the ball into the net.
Pedro Goncalves scored a magnificent equaliser for the visitors just past the hour-mark as he spotted home goalkeeper Aaron Ramsdale off his line and struck a shot from just inside the Arsenal half, his 45-yard effort dipping into the net.
Former Tottenham Hotspur forward Marcus Edwards was one-on-one with Ramsdale but had his shot saved, before Arsenal forward Leandro Trossard had just the goalkeeper to beat in extra-time but his strike was deflected onto the post.
"I think we did enough in some periods of the game but for most of the game we were not at the level that we should be," Arsenal captain Martin Odegaard told BT Sport.
"Part of the game we did well but we didn’t play our best football. It was a tight game and it could have gone both ways.
"It is a big blow to go out of this competition, it was a big goal for us. But now we have to come back stronger and make sure we finish well in the league."
Jose Mourinho’s AS Roma held Real Sociedad to a goalless draw in Spain to seal their tie 2-0 on aggregate.
The home side dominated the chances but the Italians held them at bay with stoic defending. Roma were the inaugural Europa Conference League winners last season.
Moussa Diaby's early goal and Amine Adli’s second-half strike were enough for Bayer Leverkusen to secure a 2-0 victory at Hungarian side Ferencvaros as the German club advanced 4-0 on aggregate.
Teddy Teuma, Lazare Amani and Loic Lapoussin scored for Belgian side Royale Union Saint-Gilloise as they defeated Union Berlin 3-0 to secure a 6-3 aggregate win.
They reach the quarter-finals in their first season of UEFA competition as the German side finished with 10 men after a second booking for Janik Haberer in the closing stages.
Earlier on Thursday, Marcus Rashford scored a superb goal as Manchester United eased into the quarter-finals with a 1-0 victory at Spanish side Real Betis to seal a 5-1 aggregate win.
Betis missed a number of first-half chances before Rashford scored the winner with a 30-yard shot that arrowed into the net.
Juventus defeated 10-man Freiburg 2-0 to advance 3-0 on aggregate as Dusan Vlahovic scored from the penalty spot and Federico Chiesa added a late second.
Feyenoord thrashed Ukraine's Shakhtar Donetsk 7-1 to progress 8-2 on aggregate as captain Orkun Kokcu and forward Oussama Idrissi each scored twice.
Record six-times Europa League winners Sevilla advanced despite a 1-0 loss to Fenerbahce, going through 2-1 on aggregate. Enner Valencia converted a penalty for the Turkish side.