Rangers will take on Jose Mourinho’s Fenerbahce in the UEFA Europa League last 16, while Manchester United face Real Sociedad.
United last won this competition under Mourinho in 2016/17, having last made the final in 2020/21, losing under Ole Gunnar Solskjaer.
And despite their struggles domestically, Ruben Amorim’s side will be hopeful of a strong run in the competition, having enjoyed an unbeaten league phase which saw them finish comfortably in the top eight.
United and Sociedad met in the Europa League in 2022, with the La Liga side claiming a 1-0 victory over the Red Devils – thanks to a Brais Mendez penalty.
Meanwhile, Tottenham Hotspur, who are looking to end a trophy drought stretching back to 2008, will meet AZ Alkmaar.
The two sides have already met this season in the league phase, as a Richarlison goal sealed a , and a crucial three points as they went on to seal an automatic knockout spot.
Spurs boss Ange Postecoglou had his side plagued with injury issues during their league phase run, but will be welcoming key members of his squad back to fitness for their knockout stage campaign, as the Australian hunts his first piece of silverware in the hot-seat.
Both United and Spurs will see glory in this competition as their only hope of qualifying for next season’s UEFA Champions League, given their lowly current Premier League positions of 15th and 12th, respectively.
The meeting between Rangers and Fenerbahce looks set to prove an intriguing encounter, and should Mourinho get past the challenge posed by the Scottish giants, he could face former club AS Roma in the quarter-final – where he recently spent two-and-a-half years in charge.
United, meanwhile, will face either FCSB or Lyon in the quarter-finals if they beat Sociedad across two legs. They could clash with former boss Mourinho in the semi-finals, should both the Red Devils and Fenerbahce make it that far.
Spurs, meanwhile, will face either Ajax or Frankfurt in the quarter-finals, where memories of Spurs’ stunning UEFA Champions League semi-final comeback victory over the Dutch giants in 2019 could come to the fore.
Lazio – who finished atop the league phase standings, meet Viktoria Plzen in the last 16, with a quarter-final tie against either Bodo/Glimt or Olympiacos in wait.
The seeded teams – those who finished in the top eight places of the league phase – will have home advantage in the second leg. Ties take place on March 6 and 13.
UEFA Europa League last 16 draw
The draw is split into two halves of a bracket – silver and orange – which determines each team’s route to the final.
Silver:
- Bodo/Glimt v Olympiacos
- Viktoria Plzen v Lazio
(winners of the above ties will face off in quarter-finals)
- AZ Alkmaar v Tottenham
- Ajax v Frankfurt
(winners of the above ties will face off in quarter-finals)
Orange:
- Fenerbahce v Rangers
- Roma v Athletic Club
(winners of the above ties will face off in quarter-finals)
- FCSB v Lyon
- Real Sociedad v Manchester United
(winners of the above ties will face off in quarter-finals)
Ties take place on March 6 and 13.