Manchester United have been handed a difficult tie against LaLiga leaders Real Sociedad in the last 32 of the UEFA Europa League.
Having dropped into the competition following their early elimination from the Champions League, Ole Gunnar Solskjaer and his team now face a far from ideal tie against a side that currently tops the Spanish league on goals scored.
Arsenal also received a tricky last-32 tie against Portuguese giants Benfica in an outcome that will heap more pressure on their manager Mikel Arteta following poor domestic results. Jose Mourinho’s Tottenham were handed a favourable draw against the Austrian side Wolfsberger, who have never advanced this far in Europa League football before.
The home second leg of Tottenham’s tie will be played 24 hours before the others on Wednesday February 24 because of a ‘city clash’ with Arsenal’s tie that means two games in the same area can’t be played on the same night.
Leicester City will be satisfied with their draw against Slavia Prague as they aim to make Europa League progress. Rangers were paired with the Belgian club Royal Antwerp, who finished behind Spurs in the group phase.
The first leg matches will be played on Thursday February 18 with the return matches, except Tottenham’s, on Thursday February 25. United were under the management of David Moyes when they last played Sociedad in the group stages of the 2013-14 Champions League.
They won 1-0 at Old Trafford before drawing 0-0 in Spain. Arsenal haven’t faced Benfica since the 1991-92 European Cup, when the Portuguese side beat them 4-2 on aggregate.
In other stand-out ties, AC Milan will take on Red Star Belgrade, Napoli play Granada and Lille play Ajax. Villarreal have been matched with Red Bull Salzburg, Bayer Leverkusen play Young Boys and Hoffenheim take on Molde.