Europa League Draw: Arsenal will be hoping to get their hands on this trophy in May
The Gunners - who suffered a scare to progress against Ostersunds in the round of 32 - will travel to the San Siro for the first leg on Thursday, March 8.
The second leg takes place at the Emirates Stadium the following week on Thursday, March 15.
It is the standout tie of the last-16 but Arsene Wenger will be hoping his side have enough in the tank to progress to the quarter-final stage.
Meanwhile, Chelsea loanee Michy Batshuayi will face Salzburg after Borussia Dortmund drew the Austrian club.
Express Sport brought you all the action from Nyon including the last-16 draw in full.
Europa League last-16 draw
AC Milan vs Arsenal
12.25: So Arsenal are drawn against AC Milan.
It could have been worse but it could have been better.
It might initially look like a tough tie for Arsenal but Milan aren’t the dominant force of Italian football they once were.
They are currently seventh in the Serie A table with 41 points from 25 games - 25 points behind leaders Napoli.
Last summer’s splurge in the transfer market hasn’t quite paid dividends but they’re starting to hit some form under Gennaro Gattuso.
Europa League last-16 draw
Dynamo Kiev vs Lazio
Leipzig vs Zenit
Atletico Madrid vs Lokomotiv Moscow
CSKA Moscow vs Lyon
Marseille vs Athletic Bilbao
Sporting Lisbon vs Plzen
Borussia Dortmund vs Salzburg
AC Milan vs Arsenal
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Arsene Wenger has found salvation in his remarkable Wembley record — and desperately needs another big result there this weekend.
Incredibly, Arsenal have been victorious in their last nine showpiece games at the national stadium in the FA Cup and Community Shield, always managing to rise to the big occasion.
Even more tellingly, in the FA Cup finals in 2014 and 2017, Wenger was at the end of contracts. He knew defeat would leave the fans screaming for him to go and yet somehow pulled off a result under the most severe pressure.
Arsenal went 2-0 down to Hull four years ago and you could see the nerves jangling before they came back to win and history repeated itself last May when they upset the odds to beat newly-crowned champions Chelsea.
(Image: Getty)
(Image: The FA via Getty)
(Image: Getty)
Now with his future firmly in the balance again, Wenger must get another result with the pressure on and this time it is the Carabao Cup final offering him a lifeline.
Make no mistake, Sunday's meeting with title-bound Manchester City is win-or-bust for Arsenal.
A trophy guarantees his future, finishing empty-handed and also failing to reach next season’s Champions League would increase the chances of the Frenchman leaving this summer.
Once again, Arsenal go into this final as underdogs, especially after the dismal 2-1 defeat to Swedish minnows Ostersund in the Europa League on Thursday night.
(Image: Getty)
(Image: Birmingham Mail)
(Image: Twitter/@bbcsport_david)
As reward for their 4-2 aggregate victory, they have been handed a tough last-16 draw against AC Milan in the competition that surely represents their best hope of a return to the Champions League as its winners.
Arsenal have their backs against the wall but, in fairness, that is when Wenger has been at his best — and now he faces a huge test against the best team in the country.
“The pressure is immense always, yes — last year, it was immense,” said Wenger.
“You must have enough belief to think you can do it, that on the day you managed to turn up with the right spirit and right mentality, the right belief.
(Image: Action Images via Reuters)
(Image: Arsenal FC via Getty)
(Image: AFP/Getty)
“The final, everyone says you have to be motivated. But it also finding the right balance between focus and motivation and being relaxed enough to play your game. That will be the target again: to have a belief but to find that right balance.
“We are maybe underdogs but we have to believe in our quality. The history, the fact we have done it before, shows 'Why not do it again?'"
Facing a crisis is nothing new to Wenger, but it does feel as if the walls are closing in again.
Arsenal are stuck in sixth, despite the January arrivals of Pierre-Emerick Aubameyang and Henrikh Mkhitaryan to boost their attack, the fans are restless and only a trophy can change the mood.
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poll loading Who will win the Carabao Cup final? 9000+ VOTES SO FAR Manchester City Arsenal
Wenger has never won the League Cup, but defended his record having won the FA Cup a record seven times and was clearly narked at questions about how good City counterpart Pep Guardiola is as a manager.
The 68-year-old, who nearly signed Guardiola as a player at the end of his career when he left Barcelona and flitted between clubs in Italy, Qatar and Mexico, said: “Trophies are very difficult to win.
“The simple fact is nobody has won it (the FA Cup) more than us."
Having clearly done his research, Wenger added: “Look at the big clubs. For example, Liverpool is a big club.
“How many times have they won the FA Cup in their whole history? Seven. It shows that, through history, it is not easy to win.
“I don’t want to make this about Pep Guardiola. I think what is important for us is to focus on our game.
“He has done very well in his career and he is a good manager, but what is important for us is to focus not on what is going on at Manchester City.”
When asked whether Guardiola had set a new standard this season, Wenger replied: “No, because you look at Barcelona and they are still the best team in Europe.
(Image: Getty)
“I think you have to accept that the modern game has changed with the recruitment of the best players in a small number of clubs.
“We, as managers, can maybe impart our philosophy but this game belongs to the players because the importance of the players has become bigger than ever before.
“The recruitment of the best players is in a very small number of units.”
This final could be Wenger’s last stand, both as Arsenal manager and in his fight for his footballing principles.
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