NEW DELHI: The UEFA Europa League round of 16 draw on Friday saw
Manchester United paired with Spanish side Real Sociedad. Rangers will face Fenerbahce, managed by Jose Mourinho, while Tottenham Hotspur will compete against AZ Alkmaar.
United, under Ruben Amorim's leadership, secured their place in the knockout stages after finishing third in the league phase, despite their Premier League struggles this season.
The first leg will be played in San Sebastian on March 6, followed by the return leg a week later.
Real Sociedad advanced to this stage after defeating Danish team Midtjylland in the play-off round.
The clubs share a rich history of European encounters.
United prevailed in a 2021 Europa League knockout phase play-off, followed by both teams securing away victories in the 2022/23 group stage. They also met in the 2013 Champions League group stage.
The winner of the tie will progress to face either Lyon or FCSB in the quarter-finals. FCSB recently lost 2-0 at home to United in their final group phase match.
Rangers will travel to Istanbul for their first leg against Fenerbahce. Mourinho has previous success in this competition, winning it with Manchester United in 2017 and the UEFA Cup with Porto in 2003.
A Fenerbahce victory could set up a quarter-final clash between Mourinho and his former club Roma. However, Roma faces a challenging tie against Athletic Bilbao, who are eager to reach the final at their home stadium, San Mames, on May 21.
Tottenham's tie begins with an away leg in the Netherlands against AZ, whom they previously defeated 1-0 in the group phase.
The winner of the Tottenham-AZ tie could face another Dutch journey in the quarter-finals, meeting either Ajax or 2022 champions Eintracht Frankfurt.
While Manchester United and Tottenham can only meet in the final, United could potentially face Mourinho's Fenerbahce or Rangers in the semi-finals.
Greek side Olympiakos, last season's Conference League champions, will compete against Norwegian champions Bodo/Glimt. The victor will advance to face either group phase winners Lazio or Czech Republic's Viktoria Plzen in the quarter-finals.