Up until now, the Gunners had been coming up with easy opponents and despite performing poorly away from home they were able to swing the ties in their favour at the Emirates.
Napoli have confirmed trio Lorenzo Insigne, Vlad Chiriches and Amadou Diawara will be out for the next three weeks with injury - with all potentially missing the Europa League quarter final first leg against Arsenal. Four very interesting quarter-final ties, with Arsenal v Napoli looking to be the clash of the round.
With Spain lacking their usual dominating presence in the latter stages of UEFA's two premier club competitions, few domestic advocates will have been too overjoyed with Villarreal and Valencia being drawn together in the Europa League quarter-final.
Before Arsenal can even begin to think about the semis, they will need to direct all their energies towards overcoming the team now second in Serie A. Here's what they can expect from Carlo Ancelotti and co in the quarter-finals.
"In fact I think he's been very good for Chelsea since he's been at the club, possibly underrated in many respects but proving it again in the Europa League that he can score goals".
Jovic is now on a two-year loan at the German side from their Europa League opponents Benfica, with Frankfurt likely to take up the option-to-buy clause in the summer.
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Elsewhere, Napoli wrapped up a 4-3 aggregate victory over last season's semi-finalists Salzburg despite a 3-1 second-leg loss in Austria.
"And second, it means that Naples are in the final and I am happy".
Let's take a quick look at the teams involved.
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Maurizio Sarri has opted to use some of his fringe players in the Europa League, but it remains to be seen whether that changes as they progress in the competition.
The ex-Arsenal star kept quiet about what the future may hold for him but reiterated that he was happy to have helped Chelsea advance to the final eight of the Europa League.