Manchester United will face AC Milan in the last-16 of the Europa League, while Arsenal have been paired with Olympiakos and 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.
The standout fixture in the last-16 draw is unquestionably Manchester United’s meeting with AC Milan.
That contest will see Rossoneri striker Zlatan Ibrahimovic reunited with his former club, with the evergreen Swede still going strong at 39 years of age.
He was part of the last Red Devils squad to land a trophy, under Jose Mourinho in 2017, but played no part in the Europa League final that year due to injury.
Milan will be hoping he can inspire them to similar success four years on, but Ole Gunnar Solskjaer is determined to deliver major silverware in his reign at Old Trafford.
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 Olympiakos 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.
Tottenham emerged victorious in the very first staging of the UEFA Cup back in 1972 and are two-time winners of the competition.
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 by Dynamo Kiev.
Ajax , who lost to United in the 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.
Europa League last-16 draw in full
Ajax vs Young Boys
Dynamo Kiev vs Villarreal
Roma vs Shakhtar Donetsk
Olympiakos vs Arsenal
Dinamo Zagreb vs Tottenham
Man Utd vs AC Milan
Slavia Prague vs Rangers
Granada vs Molde
When will the ties be played?
The first legs of all ties at this stage will take place on March 11.
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.