AC Milan (2017/18)
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Arsenal played their all-too-familiar foes AC Milan in last season's Europa League round of 16. Six years on from their thrilling clash in the 2011/12 season it was telling of both club's fall from grace that this clash occurred in Europe's second-tier competition and not the Champions League.
Milan went into the tie in great form under new manager Gennaro Gattuso, while Arsenal were on the opposite end of the spectrum, enduring their worst season in Arsene Wenger's 22-year tenure.
The Rossoneri hosted the first leg in a tie that was highly anticipated by both sets of fans and neutrals alike.
It was the away side who got off to the better start with new recruit Henrikh Mkhitaryan opening the scoring with a deflected strike after a quarter of an hour was played at the San Siro.
Arsene Wenger's men doubled their lead on the stroke of half-time as Aaron Ramsey rounded the onrushing Gianluigi Donnarumma and slotted into an empty net. It was Mesut Özil who assisted both of the games' goals and who stole the show.
Milan started the second leg in emphatic fashion, taking the lead at the Emirates through a brilliant dipping strike from Turkish midfielder Hakan Calhanoglu. However, their belief was short-lived as England international Danny Welbeck restored Arsenal's two-goal cushion four minutes later.
Welbeck was brought down in the box by Ricardo Rodriguez and subsequently stepped up and scored the penalty.
Granit Xhaka and Welbeck added to the Italian side's misery late on, giving Arsenal an emphatic 5-1 victory on aggregate.