Arsenal will play Sporting Lisbon in the last 16 of the Europa League while Manchester United have been drawn against Real Betis.
The Gunners, who advanced to this stage as group winners, will take on the Portuguese side over two legs on March 9th and March 16th.
It remains to be seen how much importance Mikel Arteta places on the competition given his side’s position in the Premier League title race and the gruelling Thursday-Sunday schedule it will take to win it.
But they face opposition who are no strangers to north London this season as Sporting were in Tottenham’s Champions League group before Christmas.
They beat Spurs 2-0 in Lisbon and drew 1-1 at the Tottenham Hotspur Stadium but finished third in the group and headed into the Europa League play-off round, where they beat FC Midtjylland comfortably.
Manchester United’s reward for triumphing in their heavyweight clash with Barcelona in the play-off round is more La Liga opposition after being paired with Betis.
Although United have had trouble with Spanish league opposition in Europe in recent years, their landmark victory over the Catalan side makes them one of the teams to beat in the tournament they won in 2017. Betis are fifth in La Liga and finished group winners ahead of Roma.
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Jose Mourinho’s side play Real Sociedad while Juventus take on Freiburg and six-time champions Sevilla are paired with Fenerbahce.
Elsewhere, it is the battle of the Unions as Berlin take on Belgian side Saint-Gilloise, Bayer Leverkusen play Ferencvaros and Shakhtar Donetsk were drawn against Feyenoord.
West Ham will face Cypriot side AEK Larnaca in the Europa Conference League last 16.
The Hammers, who are in the thick of a Premier League relegation battle, won all six of their group games before Christmas.
They will visit Cyprus on March 9th, with the return leg at the London Stadium on March 16th.
