Manchester United eased into the last 16 with a 4-0 aggregate win over Real Sociedad but AC Milan, who’d led the Serie A until last weekend, represent a bigger test.
The Rossoneri have been inspired by the evergreen Zlatan Ibrahimovic this season, with the ex-Red Devils forward netting 16 goals in all competitions.
However Milan have not been as convincing in Europe, edging past Red Star Belgrade on away goals after their tie finished 3-3 on aggregate.
Milan have stumbled domestically over their past five games, including losing to city rivals Inter Milan 3-0 last weekend, suffering three defeats in their past five games.
United boss Ole Gunnar Solskjaer said: “The tradition and history of AC Milan, it’s a great club that we welcome and it’s a great stadium that we go to there, and we’re looking forward to it.
“Zlatan, of course, I’ve been so impressed, I’ve got to say, by how his career has gone. He had a career-threatening injury when he was here but came back from that and went to MLS, then came back to Milan and has really lifted them.
“They’re on the up and have done really well this season. I’ve been so impressed by him.”
Among the other ties, Arsenal will take on Greek powerhouse Olympiacos, while Tottenham have been drawn against Dinamo Zagreb.
Rangers will face Leicester City’s conquerors Slavia Prague, AS Roma takes on former winners Shakhtar Donetsk and Dynamo Kiev face Villarreal.
One of the remaining contenders Ajax Amsterdam have been drawn against Swiss club Young Boys, while Granada meets Norwegian outfit Molde.