Arsenal crashed out of the Europa League as Youssef El Arabi’s goal in the last second of extra-time ensured Olympiacos advanced into the round of 16 after a dramatic victory at the Emirates Stadium.
The Gunners were lacklustre and deserved nothing more than to be humbled, although the manner of the 2-1 defeat will linger long in the memory.
Pierre-Emerick Aubameyang thought he had provided the heroics having equalised in the second period of extra-time after Pape Abou Cisse’s header had taken the tie into the additional 30 minutes.
Mikel Arteta’s men had won their last three games and shown signs they were progressing following his December appointment but they were not at the races here as last season’s beaten finalists nearly exited early on.
It took Arsenal a while to find their rhythm but when they did the Olympiacos defence panicked, Ousseynou Ba booked for tripping Nicolas Pepe on the edge of the box after the winger had been slipped in by Alexandre Lacazette.
Club-record signing Pepe dusted himself off to take the resulting free-kick but it was too high to trouble Jose Sa in the visitors’ goal.
Arsenal thought they were ahead soon after as Bukayo Saka crossed for Lacazette to turn home but – unlike the goal from the same combination in Greece a week earlier – this one was ruled out for offside against the full-back.
After a first half with hardly any chances, it was Olympiacos who would stun north London as they look the lead.
Instead of igniting a response from Arteta’s side, Olympiacos took confidence from their goal and Leno had to push a Kostas Tsimikas effort behind moments later as Arsenal rocked.
Granit Xhaka dragged an effort wide just before the hour-mark but the Gunners failed to force a shot on target until the 77th minute, Pepe drawing a smart stop out of Sa, with Lacazette then spurning a fine headed chance as the rebound was worked into him.
A fine Tsimikas challenge prevented Mesut Ozil getting a shot away as the game went into extra-time, with Shkodran Mustafi limping off injured at the start of the additional 30 minutes to be replaced by Sokratis Papastathopoulos.
But it was Olympiacos substitute Masouras who would clip the top of Leno’s crossbar as the second half of extra-time got under way.
Arsenal were still largely second-best but it would be their talisman, the man who has sparked so much debate in the last week, who looked to have salvaged their European hopes.
Ozil crossed into the middle where Gabriel Martinelli contested a header and the loose ball dropped out of the sky for Aubameyang to finish with an acrobatic bicycle kick.
But, despite just six minutes remaining, it would not be the end of the drama as El Arabi swept home in the final moments to send the away fans into raptures and close a door on the chance of silverware and a path to the Champions League for Arteta and Arsenal.