The pressure firmly increased on Arsenal head coach Unai Emery after Eintracht Frankfurt came from a goal down to beat his side 2-1 at the Emirates Stadium.
Pierre-Emerick Aubameyang struck on the stroke of half-time to give the Gunners an advantage at the break, but two goals in nine second-half minutes from Daichi Kamada turned the game on its head.
Arsenal pushed in search of an equaliser, but they failed to really create anything of note as the Bundesliga side held on for a famous victory in north London, which also keeps their hopes of qualification alive.
Despite the defeat, the Gunners should still qualify for the round of 32 barring a five-goal defeat at Standard Liege on December 12, but another poor result leaves Emery firmly on the brink at the Emirates ahead of their Premier League clash with Norwich on Sunday.
Before the match, Emery called on Arsenal to produce a performance to connect with the supporters again, but with rows and rows of empty seats around the ground – including an empty away section because of ban on Eintracht Frankfurt fans by UEFA for disorder at their away game against Vitoria – there was an eerie atmosphere at the Emirates Stadium.
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Aubameyang missed a glorious chance to get the Arsenal fans off their seats in the 12th minute, heading wide from six yards after Joe Willock got in his way.
The Gunners, who suffered an injury blow in the first half with David Luiz replaced by Matteo Guendouzi, eventually took the lead at it was Aubameyang who made amends for his early miss.
The Arsenal skipper struck on the stroke of half-time, via the underside of the crossbar, to give his side a lift heading into the break.
However, Frankfurt stunned the Emirates Stadium 10 minutes after half-time when Kamada smashed in a drive from outside the penalty.
Things got even worse for the Gunners when Kamada struck again nine minutes later, smashing into the bottom corner under no pressure to give the Bundesliga side the advantage.
Arsenal, who just needed a draw to book their place in the knockout stages, could not find an equaliser as streams of home fans left the Emirates Stadium.
Those that remained greeted the final whistle with another chorus of boos as the pressure piled on head coach Emery.
