Elsewhere, Napoli lost 2-0 to Viktoria Plzen to go out 5-0 on aggregate, Lazio won by the same score against Borussia Moenchengladbach to secure their progress, and Zenit St Petersburg survived a Liverpool fightback to go through on away goals.
Bordeaux knocked out Dynamo Kiev, Newcastle overcame Metalist Kharkiv, Anzhi Makhachkala beat Hannover and Benfica knocked out Bayer Leverkusen.
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The start of the 2017-18 Premier League season is just around the corner and is shaping up to be one of the most competitive yet.
As always it is the so called “big clubs” that have splashed the most cash in the transfer window so far this summer. Manchester United or City? Arsenal or Tottenham? Who are the winners and losers of the transfer window so far?