Arsenal missed a chance to seal top spot in Europa League Group A as they lost 2-0 to PSV Eindhoven in the Netherlands on Thursday.
The result means PSV ended Arsenal’s nine-game unbeaten run.
Arsenal only needed a point to go straight through to the last 16 next March.
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But Joey Veerman’s first-time finish from 16 yards and a header by substitute Luuk de Jong – after a mistake by keeper Aaron Ramsdale on his European debut – saw the Premier League leaders lose in Europe for the first time this season.
PSV, managed by former Manchester United forward Ruud van Nistelrooy, also had three goals ruled out for offside as Arsenal were well beaten.
The Gunners need to beat Zurich in their final group game next Thursday at Emirates Stadium to guarantee a place in the last 16.
If they fail to win and PSV beat Bodo/Glimt in Norway, Arsenal will face two extra games in the knockout round playoffs, where teams that finish third in the Champions League group stage, including Barcelona, drop into.
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