Arsenal suffered a shock Europa League exit at the hands of Greek side Olympiacos after a 2-1 Extra Time loss on Thursday night.
The match was forced to go into extra time as the two sides remained tied at 1-1 on aggregate after 180 minutes of action over the two legs.
The Gunners needed to avoid defeat on the night to book a place in the next round but fell short despite leading on aggregate with seven minutes of extra time left.
Youseff El Arabi scored the all-important goal for the visitors on the 120th minute, seven minutes after Pierre-Emerick Aubameyang had equalized for the hosts with a world-class strike that canceled out Pape Cisse's 54th-minute goal.
Arsenal were the better side in the opening minutes of the match, attacking first in the second minute but Alexandre Lacazette's cross was deflected behind for a corner.
The visitors limited the Gunners to few clear chances in the opening quarter, with the first real chance coming on the 22nd minute.
Ousseynou Ba was shown a yellow card for hauling down Nicolas Pepe on the edge of the box, with the Ivory Coast international firing the resulting freekick inches over the crossbar.
Chances were far between from both sides, but it was the visitors who came close to opening the scores on the 37th minute as Mady Camara made a good run with the ball, but his shot from the edge of the penalty area went just wide of the left post.
Arsenal thought they had scored the opener on the 39th minute, but Alexandre Lacazette's effort was correctly ruled out for offside.
Leno then made a comfortable save on the 41st minute after El Arabi got himself a shooting opportunity, but the forward scuffed his shot to allow the German to make a save.
The visitors were the first to get off the blocks in the second half, launching a terrific counter-attack on the 51st minute but Dani Ceballos was well-placed to win the ball from Randelovic.
Olympiacos then shocked Emirates when they took the lead on the 54th minute as Abou Ciesse found himself at the right place to score from a corner, planting his header straight into the bottom right corner to pull his side level on aggregate.
They almost went 2-0 up three minutes later but Konstantinos Tsimika wasted a huge opportunity as he produced a shot from the edge of the box after a brilliant solo but Leno made an astonishing save with the ball headed for the top right corner.
Arsenal went all out in search of the winning goal and came close twice on the 77th minute.
First, Nicolas Pepe received a pass inside the box, controlled the ball and drilled it towards the left post, but Jose Sa made a great save to stop his effort.
The Gunners then returned a few seconds later, but Lacazette's header went miles wide of the right post.
Mikel Arteta's charges kept knocking on the visitors' door, but there was no goal as the match was forced to go into extra time.
Aubameyang then equalized for the Gunners on the 113th minute with a world-class strike, but the lead lasted only seven minutes as El Arabi scored for the visitors following poor defending to spark wild celebrations from the traveling fans.
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