Captain Pierre-Emerick Aubameyang missed a glaring chance with the last kick of the match as Arsenal crashed to a shocking Europa League defeat at the hands of Olympiakos.
Aubameyang, so often the Gunners’ saviour, looked like he had once again rescued his side from an abject showing when his superb scissor-kick – which cancelled out Pape Abou Cisse’s opener – put them in the driving seat with seven minutes left of extra time.
But the visitors punished awful set-piece defending for a second time on the night as Youssef El Arabi poked home in front of their raucous travelling fans.
And there was still time for the unmarked Aubameyang to somehow screw wide from five yards out and condemn Mikel Arteta’s side to their first defeat of 2020.
For large periods of a flat game a full-strength Arsenal XI were frustrated, frustrating and feeble in front of goal – with their first shot on target not arriving until the 77th minute.
Olympiakos were hardly buccaneering in their approach, especially considering they had lost the first leg in Athens, but carried out their gameplan perfectly to steal a famous win and progress to the last 16.
Arteta had talked in the build-up of having three routes into Europe for next season but this competition was surely his best bet of an unlikely seat at the Champions League top table.
To go out in such limp fashion will leave the manager livid – and for most of the night he was the most animated member of the Arsenal contingent.
Familiar failings were their undoing as the Greek side twice scored from set-pieces. First, Aubameyang allowed 6ft 6ins centre-back Cisse a totally free header from a corner, and then David Luiz appeared to leave a cross from a half-cleared 120th-minute corner and gift El Arabi a lunging tap-in.
Olympiakos came to defend deep and in numbers, to frustrate Arsenal and then to hopefully score from a corner. It was a strategy they pulled off impeccably.
But they must have expected an Arsenal forward line of Aubameyang, Alexandre Lacazette, Mesut Ozil and Nicolas Pepe – recruited at a cost of around £215m – to cause more problems.
The four managed just one shot on target between them before Aubameyang’s brilliant late goal that briefly had Arsenal progressing. Ozil’s cross was nodded on by substitute Gabriel Martinelli and the Gabon striker rearranged himself masterfully to crack an acrobatic effort into the back of the net.
The home fans, who greeted the full-time whistle with apathy rather than anger, roared into belated life but it was the supporters at the other end who will now have their eyes on Friday’s draw.
Arsenal looked to have done the hard part last week when they ground out a 1-0 win in Greece. After all, the club had progressed from all 17 of their European ties when winning the first leg away from home.
But from early on they looked short of ideas and moved the ball so slowly across midfield.
For all the money spent up front the most likely route to goal all night looked like coming through teenage left-back Bukayo Saka, a constant outlet, but when he did provide a beautiful cross at the end of Arsenal’s best move of the game, Lacazette was offside as he converted from close range.
Saka and Pepe – a deeply frustrating figure to watch – both put in nine crosses but they were easy to defend.
Arteta could point to decisions that did not go his side’s way – a yellow card shown to Ousseynou Ba for a foul on the edge of the area could have been red, and an offside flag that could have been raised in the build-up to Olympiakos’ winner.
But the truth is Arsenal just did not create enough to win. Arsenal had won three in a row coming into the game and this was their first defeat in 11, but there is still much to be done.
“It hurts a lot. We had a lot of intentions in this competition,” Arteta said.
“We were in control but conceded a set-piece to put us in a difficult position. We created a lot of chances and got ourselves in a good position. If you concede four goals from set-pieces in two games it makes it very difficult.”
To add injury to insult, Arsenal also lost defender Shkodran Mustafi to a hamstring problem.