Premier League leaders Arsenal will play against Sporting Lisbon in the last 16 of the Europa League while Manchester United have been drawn against Real Betis in Friday’s round of 16 draw ceremony in Nyon, Switzerland.
The Gunners, who advanced to this stage as group winners, will take on the Portuguese side over two legs on 9 March and 16 March.
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.
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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 Spanish opposition after being paired with Betis.
Although United have had trouble with Spanish opposition in Europe in recent years, their landmark victory over Barca makes them the team to beat in the tournament they won in 2017.
Betis are fifth in La Liga and finished group winners ahead of Roma.
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.
Europa League last-16 draw
FC Union Berlin (GER) – Union Saint-Gilloise (BEL)
Sevilla FC (ESP) – Fenerbahçe SK (TUR)
Juventus (ITA) – SC Freiburg (GER)
Bayer 04 Leverkusen (GER) – Ferencvárosi TC (HUN)
Sporting Clube de Portugal (POR) – Arsenal FC (ENG)
Manchester United (ENG) – Real Betis Balompié (ESP)
AS Roma (ITA) – Real Sociedad de Fútbol (ESP)
FC Shakhtar Donetsk (UKR) – Feyenoord (NED)
Europa Conference League last-16 draw
AEK Larnaca FC (CYP) – West Ham United FC (ENG)
ACF Fiorentina (ITA) – Sivasspor (TUR)
S.S. Lazio (ITA) – AZ Alkmaar (NED)
KKS Lech Poznań (POL) – Djurgårdens IF (SWE)
FC Basel 1893 (SUI) – ŠK Slovan Bratislava (SVK)
FC Sheriff Tiraspol (MDA) – OGC Nice (FRA)
RSC Anderlecht (BEL) – Villarreal CF (ESP)
KAA Gent (BEL) – İstanbul Başakşehir FK (TUR)
Sides listed first will play the first leg at home
All first legs to take place on 9 March; All second legs to take place on 16 March.