Arsenal's European dream ended following a defeat on penalties to Sporting CP in the second leg after Gabriel Martinelli missed from the spot in front of his own fans in the shoot-out.
Both teams came into the fixture on the back of a 2-2 draw in the first leg.
The hosts suffered an early blow in the game after Takehiro Tomiyasu was forced off just 9 minutes into the contest, with Mikel Arteta bringing on Ben White as his replacement.
Sporting took the game to the Gunners controlling possession and showing some good passing sequences.
Moments later, the visitors soon started to ask the questions.
Trincao found his way into the box but couldn’t place his effort on target in what was a real opportunity for Sporting to grab the opener in the 13th minute.
On the other end, Gabriel Jesus saw his shot saved by Sporting goalkeeper Antonio Adan.
The Gunners grew into the game and moments later opened the scoring with that momentum.
In the 30th minute, Gabriel Jesus saw his effort saved once more by Adan before Marcus Edwards saw his effort blocked by a defender on the other end in the 45th minute.
The final action of the first period saw a wayward effort from Manuel Ugarte as the hosts went into the break with a slender advantage.
Things got much more interesting in the second period as Sporting sought to level matters as soon as the game restarted.
Pedro Goncalves saw his attempt sail well wide of the post in the 50th minute, before Paulinho saw his short that looked goal-bound blocked by an Arsenal defender four minutes later.
However, the visitors would finally breach Arsenal’s defense in epic fashion.
Pedro Goincalves received the ball in the middle of the pitch 62nd minute and unleashed a rocket from way outside the box to fire home the leveller for the visitors and put the scores at 1-1.
Sporting gained more confidence and kept creating chances with Marcus Edwards once more in the picture, the Sporting no.10 saw his effort from close range saved by Aaron Ramsdale in the 72nd minute.
Gabriel Martinelli had a chance to restore Arsenal’s lead minutes later, but saw his freekick saved by Antonio Adan in the 79th minute, before Granit Xhaka headed wide from a corner in the 82nd minute.
Sporting remained very much in the contest but neither side could eventually find the winner after the end of 90 minutes.
With the scores being 3-3 on aggregate, both sides were forced into extra time as there could only be one winner at the Emirates.
Leandro Trossard missed a golden opportunity to perhaps give the Gunners the win after seeing his effort rattle the crossbar eight minutes into added time.
With nothing to still separate both teams at halftime in extra time, fans were hopeful of getting a winner in the final 15 minutes of the game.
Thomas Partey saw his effort sail wide of the post in the 106th minute, as Arsenal looked desperate to avoid the contest going into penalties.
12 minutes later, Antonio Adan ensured his side were still in the tie after keeping out a goal-bound header from Gabriel.
But Sporting soon suffered a setback as they were reduced to 10 men after referee Mathieu Lahos, showed Manuel Ugarte his second yellow of the night at a crucial stage for the visitors.
With nothing to still split both sides at the end of 120 minutes, the contest finally came down to penalties.
Both teams scored each of their first three penalties before Gabriel Martinelli missed for the Gunners in the fourth kick with Sporting CP scoring all their penalties and ultimately defeating the Gunners 5-3 on penalties to progress to the quarter finals of the Europa League.
Social Media Reactions
Following the result for the Premier League leaders Arsenal on Thursday night, here's how fans have reacted on social media: