Arsenal have been drawn against Sporting Lisbon in the last 16 of the Europa League, while Manchester United will meet Real Betis.
The Gunners qualified for the last 16 of the Europa League directly by finishing top of Group A above PSV Eindhoven.
They have been rewarded with a tie against Ruben Amorim’s Portuguese giants.
Having dropped down from the Champions League – finishing behind Eintracht Frankfurt and Tottenham Hotspur – Sporting were paired with Midtjylland in the knockout round playoffs and thumped the Danish side 5-1 on aggregate.
Meanwhile, Man United – who beat Barcelona 4-3 on aggregate to keep their hopes of a quadruple haul of trophies alive – will do battle with Betis, who topped Group C with 16 points from 18.
Another trip to Spain therefore awaits the Red Devils, who also did battle with Real Sociedad in the group phase before an entertaining 2-2 draw against Barcelona at Camp Nou.
Elsewhere, Man United’s previous opponents Sociedad – who beat the Red Devils to top spot in Group E on goal difference – face reigning Europa Conference League champions Roma.
Jose Mourinho’s side finished second in Group C, but they were forced to overturn a 1-0 deficit in their playoff clash with Red Bull Salzburg to win 2-1 on aggregate on Thursday night.
An intriguing battle of the Unions will also take place, as Belgian surprise package Union SG reunite with Bundesliga hopefuls Union Berlin, who impressively dispatched Ajax in the playoffs.
Union Berlin finished one point behind Union SG in the group stage, while Juventus’ success over Nantes means that the Italian giants will tackle Group G winners Freiburg.
Sevilla, who survived a late scare against PSV Eindhoven on Thursday, have been paired with Turkish giants Fenerbahce, but there is Dutch representation in the form of Feyenoord, who take on Shakhtar Donetsk.
Finally, having beaten Monaco on penalties after an enthralling 5-5 aggregate draw, Bayer Leverkusen take on Ferencvaros, who pipped the recently-eliminated French side to top spot in Group H.
The first legs of the last-16 ties will be held on March 9 before the second legs commence on March 16.
EUROPA LEAGUE LAST-16 DRAW IN FULL:
Union Berlin vs. Union SG
Sevilla vs. Fenerbahce
Juventus vs. Freiburg
Bayer Leverkusen vs. Ferencvaros
Sporting vs. Arsenal
Man Utd vs. Real Betis
Roma vs. Real Sociedad
Shakhtar Donetsk vs. Feyenoord.