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.
It will complete a sequence of five consecutive Thursday matches for Arsene Wenger’s team, including a Premier League fixture against Manchester City next week. Milan, who have never won the Uefa Cup or Europa League, beat Bulgarian club Ludogorets Razgrad 4-0 on aggregate in their last 32 tie, while Arsenal progressed 4-2 over two legs against Swedish club Ostersunds FK. This was despite what Wenger called a “complacent” first half performance in Thursday’s 2-1 second leg defeat.
Wenger is intending to play a full strength team now in the Europa League in the knowledge both that the Premier League will be their only other competition this season and also the chance to gain Champions League qualification by winning the final in Lyon on May 16.
Arsenal are currently sixth in the Premier League, eight points behind Chelsea in fourth, and know that the Europa League may become their most viable route back into the Champions League.
Jose Mourinho’s Manchester United ended last season by prioritising the Europa League after slipping outside the Premier League’s top four and that choice was ultimately vindicated with their victory in the final against Ajax. It is a bigger challenge this season for Arsenal in the context of so many other leading clubs still left in the competition.
Atletico Madrid, Borussia Dortmund and Lazio all avoided each other in the last 16 draw although Marseille will face Athletic Bilbao. Russian club Zenit St Petersburg, who knocked out Scottish champions Celtic, play RB Leipzig of Germany.
Arsenal and AC Milan have enjoyed a couple of thrilling knockout ties in the last decade.
First there was 2008 when Arsenal knocked out the Champions League holders with a 2-0 last-16 win at San Siro before Milan exacted revenge with a 4-3 aggregate win at the same stage four years later. In that 2012 meeting, Milan won the first leg 4-0 before Arsenal so nearly pulled off a miracle comeback by winning the second leg 3-0.
The first leg of this Europa League tie will be played on Thursday March 8 at San Siro, with the return a week later on March 15 at the Emirates.
UEFA Europa League Round Of 16 Draw
AC Milan v Arsenal
Borussia Dortmund v Salzburg
Sporting Lisbon v Viktoria Plzen
Marseille v Athletic Bilbao
CSKA Moscow v Lyon
Atletico Madrid v Lokomotiv Moscow
RB Leipzig v Zenit
Lazio v Dynamo Kiev
The first legs will be played on Thursday March 8 with the second legs played on Thursday March 15.
The team drawn out first will play at home first before playing the second leg away.