Match ends, Arsenal 1, Eintracht Frankfurt 2.
The pressure on Arsenal manager Unai Emery intensified as Daichi Kamada's brilliant double earned Eintracht Frankfurt victory at the Emirates Stadium.
The Gunners boss came into this Europa League match having failed to lead his team to victory in their previous six outings, and this latest defeat means this is their longest winless run since February 1992.
At full-time the Spaniard appeared to make a gesture to the sparse home support as they jeered him, with some holding 'Emery Out' posters having watched their side surrender control against a team who were a clear second best in the first period.
However, Arsenal will seal qualification for the last 32 if they avoid a heavy defeat at Standard Liege in their final Group F game.
It looked like the Gunners had turned the corner after they dominated the opening period. Eintracht spent most of it trying to keep Arsenal's attack at bay until Pierre-Emerick Aubameyang made the breakthrough with a strike just before half-time.
The Bundesliga side only managed one shot on goal in the first half, but were transformed after the break and equalised when Kamada curled in a fierce effort from the edge of the box.
The 23-year-old Japan international then put his side in front with another sweet strike from the edge of the area.
The contest also marked the return of Granit Xhaka to the Arsenal XI. The Swiss midfielder had missed the Gunners' past five matches after his infamous substitution in the 2-2 draw against Crystal Palace at the end of October, when he angrily gestured to supporters.
The 27-year-old appeared to pick up a knock to the knee in the first half but following treatment played the full 90 minutes.
Can Emery survive a seventh match without a win?
The 48-year-old, given the task of moulding a new Arsenal after succeeding Arsene Wenger in 2018, is now odds-on with some bookmakers to be the next Premier League manager to lose his job.
The Europa League had offered some respite from the difficulties of the top flight - where his side have only won four of their 13 games and are eight points adrift of the top four - but the same problems reared their head on a forgettable night at Emirates Stadium.
With Wolves manager Nuno Espirito Santo identified as a potential replacement, how many more disappointments will Arsenal's hierarchy tolerate before they finally decide to twist?
It was all smiles on the home bench in the first half, and the only issue Emery had to contend with was being told he had to change his jacket because it clashed with Eintracht's colours.
Even the 31st-minute departure of the injured David Luiz, who was playing in midfield, did not upset the Gunners' rhythm as the attack of Aubameyang, Joe Willock, Gabriel Martinelli and Bukayo Saka continually troubled the opposition backline.
Martinelli had a shot blocked and header cleared off the line while Aubameyang nodded wide before he swept home the Brazilian's low cross just before half-time.
It was the former Borussia Dortmund striker's 10th in 13 appearances against the Bundesliga club and his 31st goal in 44 home appearances for the Gunners.
However, it was a very different story for the home side in the second half.
Two substitutions by Eintracht coach Adi Hutter revitalised their attack, but his players were aided by some poor Arsenal defending.
The lively Kamada was allowed to advance towards the edge of the area by Sokratis before launching a brilliant strike past keeper Emiliano Martínez, and was then given even more space to line up his second, which found the same corner.
That was the 18th goal conceded by Arsenal in nine games.
The home attack, so potent in the first half, failed to find a response in the closing minutes as Eintracht defeated English opposition away from home for the first time since beating Burnley 2-1 in the Fairs Cup in April 1967.
Xhaka return overshadowed by defeat
Perhaps Xhaka will have been relieved that the attention was shifted from him onto his manager.
He produced a competent display in front of his backline, although perhaps could have done more in helping defender Sokratis close down Kamada for his first goal.
The injury to his knee in the first half did not appear to have affected his overall performance and he even raised a cheer from the home support when he tricked his way past an Eintracht defender to set up Calum Chambers, who fired over the bar.
The only stain was the late yellow card he picked up for dissent when he threw down the ball in frustration thinking he won a tackle cleanly.
With the injury to Luiz it could be that Xhaka retains his place for next Sunday's trip to Norwich.
Eintracht end English jinx - stats
- Arsenal have not won any of their past seven matches in all competitions (D5 L2) - they never went on as poor a run across 1,235 games under Wenger, last waiting this long for a win in February 1992 under George Graham (eight games).
- Arsenal have led in five games during their current seven-match winless run, drawing four and losing one of those five games.
- Arsenal were unbeaten in their previous 46 matches in all competitions when leading at half-time before tonight (W40 D6) since losing 2-1 at Watford in October 2017.
- Saka has assisted five goals in his nine starts for Arsenal in all competitions, three of which have come against Eintracht.
- 20MustafiBooked at 74minsSubstituted forTorreiraat 76'minutes
- 23David LuizSubstituted forGuendouziat 31'minutesBooked at 90mins
- 34XhakaBooked at 86mins
- 35MartinelliBooked at 34minsSubstituted forÖzilat 60'minutes
- 19AbrahamBooked at 59mins
- 24da Costa
- 5FernandesSubstituted forKohrat 45'minutes
- 10KosticBooked at 20mins
- 33André SilvaSubstituted forGacinovicat 45'minutes
- 39Mendes PaciênciaBooked at 90mins
- Ruddy Buquet
- Shots on Target
Second Half ends, Arsenal 1, Eintracht Frankfurt 2.
Foul by Lucas Torreira (Arsenal).
Daichi Kamada (Eintracht Frankfurt) wins a free kick in the defensive half.
Joe Willock (Arsenal) wins a free kick on the left wing.
Foul by Daichi Kamada (Eintracht Frankfurt).
Gonçalo Paciência (Eintracht Frankfurt) is shown the yellow card.
Attempt missed. Gonçalo Paciência (Eintracht Frankfurt) right footed shot from the centre of the box is close, but misses to the right. Assisted by Danny da Costa.
Matteo Guendouzi (Arsenal) is shown the yellow card for a bad foul.
Foul by Matteo Guendouzi (Arsenal).
Mijat Gacinovic (Eintracht Frankfurt) wins a free kick in the attacking half.
Attempt blocked. Bukayo Saka (Arsenal) left footed shot from outside the box is blocked. Assisted by Mesut Özil.
Corner, Arsenal. Conceded by Daichi Kamada.
Corner, Arsenal. Conceded by Dominik Kohr.
Granit Xhaka (Arsenal) is shown the yellow card.
Foul by Granit Xhaka (Arsenal).
Gonçalo Paciência (Eintracht Frankfurt) wins a free kick on the right wing.
Matteo Guendouzi (Arsenal) wins a free kick in the defensive half.
Foul by Dominik Kohr (Eintracht Frankfurt).
Hand ball by Gonçalo Paciência (Eintracht Frankfurt).