Manchester United was paired with Spanish league leader Real Sociedad in the round of 32 of the Europa League on Monday.
United will play away first against Sociedad, which has been inspired this season by former Manchester City playmaker David Silva’s homecoming to Spain.
In Monday’s draw, Arsenal got a tough pairing with Benfica, which also went unbeaten through the Europa League group stage.
Arsenal, struggling at 15th place in the English Premier League, was the only team to win six group-stage games while Benfica finished runner-up to Rangers.
Seven-time European champion AC Milan was paired with 1991 European Cup winner Red Star Belgrade.
The Europa League knockout stage includes third-place teams — such as Man United — from the Champions League group stage.
Among the others, Ajax was drawn away to Lille, and Shakhtar Donetsk travels to face Maccabi Tel-Aviv.
Dynamo Kyiv will face Club Brugge in a pairing of two Champions League teams.
First-leg games are on Feb. 18 and return games are one week later.
The final is scheduled May 26 in Gdansk, Poland.
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