Manchester United and Arsenal have been paired to face AC Milan and Olympiacos respectively in the last 16 of the Europa League.
Another Premier League club, Tottenham will take on Dinamo Zagreb.
Steven Gerrard’s Rangers must overcome Slavia Prague in order to prolong their continental adventure and Serie A giants Roma face a tough task against Shakhtar Donetsk.
Manchester United’s Premier League rivals Arsenal will also consider themselves to be strong contenders to go all the way.
They survived a scare against Benfica in the last 32, as a late goal from Pierre-Emerick Aubameyang saw them through, and will need no reminding that they slipped out of the Europa League at that stage to Olympiacos last season – with that rivalry about to be rekindled.
Spurs boss Mourinho boasts plenty of pedigree in European competition and, ahead of a meeting with Dinamo Zagreb, has already guided his side into the Carabao Cup final this season.
Rangers came close to getting their hands on that trophy back in 2008, as they booked a final date with Zenit, but suffered defeat on that occasion and will want to dispose of Slavia Prague en route to another showpiece event.
Elsewhere, Roma are unlikely to have things all their own way against Shakhtar Donetsk, and Villarreal can expect a stern test of their credentials against Dynamo Kyiv.
Ajax, who lost to United in 2017 final, will hope to have too much for Swiss outfit Young Boys and two debutants at this stage of the Europa League will lock horns in the form of Granada and Molde.
Here is the Europa League last-16 draw in full:
- Ajax vs Young Boys
- Dynamo Kyiv vs Villarreal
- Roma vs Shakhtar Donetsk
- Olympiacos vs Arsenal
- Dinamo Zagreb vs Tottenham
- Man Utd vs AC Milan
- Slavia Prague vs Rangers
- Granada vs Molde
The first legs of all ties at this stage will take place on March 11, while the return dates will be held a week later on March 18.
All of those left in the competition are chasing down a final spot in Gdansk on May 26.
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