Tottenham have been drawn against Wolfsberger in the last 32 of the Europa League, while Manchester United will face Real Sociedad.
Jose Mourinho’s side will head to Austria in February having won Group J.
Manchester United will head to Real Sociedad for the first leg of their last-32 tie having been paired together after United were knocked out of the Champions League last week.
Arsenal will play Benfica with Mikel Arteta’s side having topped Group B.
Rangers will play Royal Antwerp, with Steven Gerrard’s side having won Group D ahead of Benfica.
Leicester have been drawn against Slavia Prague in the last 32 and will travel to the Czech Republic for the first leg.