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, which is live on Sky Sports.
- Senior Arsenal figures to discuss poor form
- Emery on defeat: I think we improved
- Europa League tables | Results
Arsenal: Martinez (6), Mustafi (5), Sokratis (5), Luiz (5), Chambers (5), Xhaka (6), Willock (5), Tierney (6), Martinelli (6), Saka (6), Aubameyang (6).
Subs: Guendouzi (5), Ozil (5), Torreira (5)
Eintracht Frankfurt: Ronnow (7), Abraham (7), Hasebe (7), Hinteregger (8), Da Costa (7), Kamada (8), Fernandes (6), Sow (7), Kostic (7), Silva (6), Paciencia (7)
Subs: Gacinovic (7), Kohr (7).
Man of the match: Daichi Kamada
How the pressure piled on Emery
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.
Granit Xhaka returned to Gunners' starting-line up for the first time since he was booed by his own fans after being substituted during the 2-2 draw with Crystal Palace last month.
On the whole he was given a good reception from the Arsenal supporters. His name was greeted with a mixture of jeers and cheers before kick-off but he was given an excellent ovation when he left the field after an injury scare.
In the second half, he drew a huge roar from the Emirates with an excellent piece of skill before creating an opportunity for Calum Chambers. Small steps, but a positive night for the former captain, if not the team.
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.
Unai Emery recalled former captain Granit Xhaka into the Arsenal side to face Eintracht Frankfurt. The midfielder has not played for the Gunners since being stripped of the armband after swearing at supporters following his substitution during a 2-2 draw at Crystal Palace on October 27. But he was included for the Group F match as Emery seeks a first win in six games, with five of the team who started the 2-2 draw against Southampton retaining their places.
Sokratis Papastathopoulos, David Luiz and Calum Chambers stayed in the side, as did Kieran Tierney and new captain Pierre-Emerick Aubameyang. Emiliano Martinez, Shkodran Mustafi, Joe Willock, Bukayo Saka and Gabriel Martinelli also came in.
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.
What the manager said
Arsenal boss Unai Emery: "I think we improved. In the first half we had control of the game and we were winning 1-0 but we created chances to score a second goal.
"The first five or 10 minutes or so of the second half was positive, how we were playing. We lost control in 15 minutes of the second half and they scored two goals and then we couldn't change the result.
"The last 20 minutes we tried to come back but we didn't create in that moment a big opportunity to score."
Analysis: It all looked muddled again
Sky Sports' Oliver Yew at the Emirates Stadium…
"'Emery Out. No tactics, no formation, nowhere to hide.'
"Those were the words visible on a banner held aloft by frustrated Arsenal fans during the second half as the Gunners suffered yet another setback under Unai Emery - and it's very difficult to disagree.
"There were yet more tactical changes from Emery as he shifted David Luiz into a holding midfield role - an experiment which ended when the Brazilian was forced from the field because of injury early in the match.
"Despite leading at half-time, the Gunners again lacked direction and looked void of any sort of confidence throughout the game, which was played in front of a sparse crowd at the Emirates Stadium.
"The manager was continuously barking orders from his technical area but on the pitch it all looked muddled once again, and the Gunners never really looked like finding a way out once Eintracht Frankfurt levelled things up.
"Panic then set in as Arsenal's defending cracked under the pressure. It seemed inevitable that Frankfurt would go on to score a second and the inevitable happened as Kamada was given the freedom of north London on the edge of the Arsenal box before finding the bottom corner.
"The tension was building amongst the home fans and it hit a crescendo as the final whistle condemned Emery's men to their worst run since 1992. Despite the sparse crowd, the boos were loud. They were making their feelings known loud and clear - and it's time for the powers that be to listen.
"Decisive is not generally a word associated with the decision makers at the Emirates Stadium, but they need to take control of this situation before it's too late."
- Arsenal have not won any of their last seven matches in all competitions (D5 L2) - they never went on as poor a run across 1,235 games under Arsene Wenger, last waiting this long for a win in February 1992 under George Graham (8 games).
- Arsenal have led at any stage in five games during their current seven-match winless run, drawing four and losing one of those five games after going ahead.
- Eintracht Frankfurt have defeated English opposition away from home in Europe for the first time since beating Burnley 2-1 in the Fairs Cup in April 1967.
The draw for the last 32 of the Europa League takes place on Monday, December 16 in Nyon, with proceedings set to start at 12pm, UK time.
Arsenal travel to Norwich on Sunday at 2pm in the Premier League, live on Sky Sports, while their last Europa League group-stage clash is at Standard Liege on December 12 at 5.55pm.