Arsenal drew another continental heavyweight at the last 16 stage of a European competition yesterday when they were paired with Italian club AC Milan in the Europa League.

Milan have won the European Cup seven times and, over the past eight years, Arsenal have now faced Barcelona, Bayern Munich or Milan in all but one season at this point of the knockout phase.

Arsenal have also always failed to progress past the last 16 since 2010, losing 4-0 at the San Siro before winning the return 3-0 in an ultimately futile second leg victory six years ago.

They should have a better chance this season, with Milan currently seventh and some 25 points adrift of Napoli in Italy’s Serie A despite spending around £200 million last summer. Milan have also not won Serie A since 2011 and finished only sixth last year, although former midfielder Gennaro Gattuso has overseen an improvement since his appointment as manager last November.

Arsenal must travel to Italy for the first leg on March 8 and will then host Gattuso’s team for the second leg at the Emirates on March 15.