Arsenal finished runners up in the Champions League's so-called 'Group of Death' after losing away to Napoli 2-0 on Wednesday evening.
The hosts took the lead in the 73rd minute after Napoli striker and former Arsenal target Gonzalo Higuaín received the ball from outside the box and smashed it past Arsenal 'keeper Wojciech Szczesny in impressive style.
The second goal came in injury time after summer signing Jose Callejón - formerly of Real Madrid - chipped the ball over Szczesny to secure the win for Napoli.
However, the win was not enough for Napoli to progress into the last 16, with Borussia Dortmund having beaten Marseille 2-1. Dortmund midfielder Kevin Großkreutz scored three minutes from time to send Dortmund to the top of Group F on goal difference.
Arsenal went down to 10 men after Spanish midfielder Mikel Arteta received his second yellow card of the evening.
Arsenal had the chance to take the lead in the 23rd minute after Mathieu Flamini's pass was met by Olivier Giroud, but his shot was saved by Napoli keeper Rafael. Arsenal then nearly gave Napoli the lead when Szczesny received a back pass from Laurent Koscielny and kicked the ball straight at Higuaín, who headed into the side netting.
What this result means for Arsenal is that they will face either Real Madrid, Barcelona, Paris St-Germain, holders Bayern Munich or Atletico Madrid in the last 16, whilst Borussia Dortmund will face either Galatasaray, AC Milan, Zenit St Petersburg or Olympiakos.
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