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Manchester United will face Real Sociedad in the Europa League last 16, while Tottenham play AZ Alkmaar and Rangers take on Jose Mourinho's Fenerbahce.
Last-16 ties will begin on March 6 with the second legs on March 13.
Man Utd and Spurs can only meet in the final but United could play Rangers in the semi-finals or have a reunion with their former manager Mourinho.
Tottenham sacked Mourinho in April 2021, less than a week before they were due to play in the Carabao Cup final, and can only face Fenerbache in the final.
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Man Utd were the only team to complete the league phase unbeaten and finished third while Real Sociedad reached the last 16 with a 7-3 victory on aggregate over Midtjylland.
Spurs have already faced AZ Alkmaar, securing a 1-0 victory on their way to finishing fourth before the Dutch side earned an impressive 6-3 win on aggregate over Galatasaray in the knockout play-offs.
Rangers sneaked through in the final automatic place and now face Fenerbahce, who made the last 16 the hard way finishing in 24th and then beating Anderlecht 5-2 on aggregate.
Europa League last-16 draw
Bodo/Glimt vs Olympiacos
Fenerbahce vs Rangers
Ajax vs Eintracht Frankfurt
FCSB vs Lyon
AZ Alkmaar vs Tottenham
Real Sociedad vs Man Utd
Viktoria Plzen vs Lazio
Roma vs Athletic Bilbao
Man Utd's route to the Europa League final
Last 16: Real Sociedad
Quarter-final: Lyon or FCSB
Semi-final: Fenerbahce, Rangers, Roma or Athletic Bilbao
Final: Viktoria Plzen, Lazio, Olympiakos, Bodo/Glimt, Frankfurt, Ajax, AZ Alkmaar or Tottenham
Tottenham Hotspur's route to the Europa League final
Last 16: AZ Alkmaar
Quarter-final: Ajax or Frankfurt
Semi-final: Viktoria Plzen, Lazio, Olympiakos or Bodo/Glimt
Final: Real Sociedad, Man Utd, FCSB, Lyon, Fenerbahce, Rangers, AS Roma or Athletic Bilbao
Rangers' route to the Europa League final
Last 16: Fenerbahce
Quarter-final: Athletic Bilbao or AS Roma
Semi-final: Real Sociedad, Man Utd, FCSB or Lyon
Final: Viktoria Plzen, Lazio, Olympiakos, Bodo/Glimt, Frankfurt, Ajax, AZ Alkmaar or Tottenham
When are the Europa League knockout rounds?
- Last-16 games will be played on March 6, with the second legs taking place on March 13.
- The quarter-finals are on April 10, with the return legs on April 17.
- The semi-finals will take place on May 1, with second legs on May 8.
- The final will be played at the Estadio de San Mames in Bilbao, Spain, on May 21.
Europa League knockout play-offs fixtures and results
First legs
Feb 13: Midtjylland 1-2 Real Sociedad
Feb 13: Fenerbahce 3-0 Anderlecht
Feb 13: Ferencvaros 1-0 Viktoria Plzen
Feb 13: Union Saint-Gilloise 0-2 Ajax
Feb 13: AZ Alkmaar 4-1 Galatasaray
Feb 13: Porto 1-1 Roma
Feb 13: Twente 2-1 Bodo/Glimt
Feb 13: PAOK Salonika 1-2 FCSB
Second legs
Feb 20: Bodo/Glmit 5-2 Twente (agg 6-4)
Feb 20: FCSB 2-0 PAOK Salonika (agg 4-1)
Feb 20: Galatasaray 2-2 AZ Alkmaar (agg 3-6)
Feb 20: Roma 3-2 Porto (agg 4-3)
Feb 20: Ajax 1-2 Union Saint-Gilloise (agg 3-2)
Feb 20: Anderlecht 2-2 Fenerbahce (agg 2-5)
Feb 20: Viktoria Plzen 3-0 Ferencvaros (agg 3-1)
Feb 20: Real Sociedad 5-2 Midtjylland (agg 7-3)
(c) Sky Sports 2025: Europa League last-16 draw: Man Utd, Tottenham Hotspur and Rangers discover opponents and route to final