Arsenal were made to wait for Europa League qualification after surrendering the lead as Eintracht Frankfurt came from behind to win 2-1 at the Emirates.
Under pressure Unai Emery recalled former captain Granit Xhaka who hasn’t played since 27 October after swearing at fans as he was subbed off at Crystal Palace.
New club skipper Pierre-Emerick Aubameyang gave the Gunners the lead on the stroke of half time as Arsenal dominated the first half.
The second half was very different though. Daichi Kamada brought Frankfurt back on terms ten minutes after the restart with a lovely turn and finish from outside the box before firing the German side in front with another precise finish nine minutes later.
Boos rang around the stadium at the full-time whistle as Arsenal have now gone seven games without a win. The first time they have had such a run since 1992.
A draw would have been enough to see Arsenal progress to the round of 32, but they’ll now have to wait until their final group game at Standard Liege on 12 December.
Unai Emery recalled former captain Granit Xhaka who hasn’t played for the Gunners since being stripped of the armband after swearing at supporters following his substitution during their 2-2 draw at Crystal Palace on 27 October.
The Arsenal manager made a further five changes from their 2-2 draw against Southampton at the weekend as they looked for a first win in six games.
The hosts should have taken the lead after 11 minutes after some lovely work from Bukayo Saka on the left.
He disposed of three players before putting a perfect ball into the box, but confusion between Pierre-Emerick Aubameyang and Joe Willock saw a glorious chances headed wide by the striker.
The Gunners were then almost gifted the lead five minutes later after Gabriel Martinelli found the ball at his feet from a defensive header. He was unmarked but his effort was pushed behind superbly by Frederik Ronnow.
From the resultant corner, Martinelli's header was cleared off the line by Gelson Fernandes.
Shortly before the break Willock and Saka linked up nicely to forge a chance for the home side but the 18-year-old’s low drive was denied by Ronnow.
The hosts took the lead in the final minute of the half through captain Aubameyang. Saka played it out wide to Martinelli, who squared into the box, Saka left it and Aubameyang found the back of the net through the underside of the crossbar.
Xhaka almost made it 2-0 just before half time as he popped up on the edge of the box to meet a cross but scuffed his effort wide.
The visitors started the second half brightly and were level in the 55th minute through Daichi Kamada.
The Japanese international received the ball with his back to goal, turned and smashed a low drive into the bottom corner to make it 1-1.
Things went from bad to worse nine minutes later for Arsenal as Kamada then put Frankfurt in front.
Xhaka’s headed clearance only went as far as the 23-year-old who had time to pick his spot and he fired into the bottom corner from the edge of the box once more.
With two minutes left on the clock Saka went down inside the penalty area after Filip Kostic flicked the ball away and the referee waved away any claims of a spot kick.
Arsenal lacked any real fight to get back into the match and the pressure will be mounting on their manager Unai Emery after another defeat.
A draw would have been enough to see them progress into the round of 32.
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