Manchester United were drawn against Paris Saint-Germain in the round of 16 of the Champions League.
Liverpool will face Salzburg for the first time in the Champions League round of 16, Chelsea will face Ligue 1 champions Lille, while Manchester City will face reigning Europa League winners Villarreal.
Other major challenges include Atletico Madrid against Bayern Munich, while Serie A winners Inter will face Ajax, who enjoyed a perfect campaign in the group stage.
Sky Sports News asked UEFA to clarify what happened with the Atletico Madrid draw and why Manchester United were not put in the pot as an option for the draw.
United were also originally pulled out of the hat incorrectly to face Villarreal. The pair met in the group stage, so it should have been kept apart.
With the scoreboards, the choice of the group sees Mauricio Pochettino going to Old Trafford for the return match in March. The PSG coach has been identified as the managerial goal n. 1 for United this summer after Ole Gunnar Solskjaer was sacked and before Ralf Rangnick took over as interim.
The match also sees Cristiano Ronaldo versus Lionel Messi in the round of 16, their first showdown since Barcelona faced Juventus in the group stage last year.
Ronaldo was pivotal for United leading Group F, scoring six times including two late winners, while PSG finished second behind City in Group A.
United last played with PSG in the 2020-21 group stage, winning 2-1 in Paris before losing 3-1 at Old Trafford.
The two sides also met in the round of 16 in 2019, which was arguably the highlight of Solskjaer’s spell when a Marcus Rashford penalty in injury time helped United advance 3-3 on aggregate.
Liverpool became the first English team to win all six Champions League group stage games
Meanwhile, Liverpool’s reward for becoming the first English team to win all six Champions League group games is a draw with Austrian side Salzburg, who finished second behind Lille in Group G.
Liverpool played against Salzburg in the 2019-20 group stage, winning a 4-3 thriller at Anfield before a 1 2-0 win in Austria.
Two years ago, defending champions Chelsea also faced their opponents in the round of 16 in the groups, winning both games against Lille 2-1.
Chelsea had to settle for second place in Group H after drawing 3-3 with Zenit in their last group match
An error initially saw United drawn to play against Villarreal, but after it was corrected as both teams played against each other in groups, it was the name of the City chosen to face Villarreal.
City, last season’s losing finalist, have faced Villarreal only twice, in the 2011-12 group stage, winning 2-1 at home and 3-0 away.
Manchester City advanced to the round of 16 as group winners ahead of PSG
Champions League round of 16 draw
Benfica-Real Madrid
Villarreal v Manchester City
Atletico Madrid-Bayern Munich
Salzburg vs Liverpool
Inter-Ajax
Sporting Lisbon-Juventus
Chelsea vs Lille
Paris Saint-Germain-Manchester United
A 180-minute job interview for Pochettino?
Mauricio Pochettino’s PSG faced Man City in the group stage
European football expert Andy Brassell on Sky Sports News:
“That would be a difficult interview. You can’t expect him to show up and change the company mind in 10 minutes – it’s just too much.
“I don’t think there are the conditions for Pochettino to reach the level of success he wants to achieve and to establish himself at PSG.
“There is now an understanding on this. I would be amazed if they win the Champions League.”
When is the round of 16?
The matches of the round of 16 will be divided into several weeks, with the first legs scheduled for February 15-16 and February 22-23.
The second stages are then on March 8-9 and March 15-16.
What are the key dates?
Last 16 first leg matches: 15/16/22/23 February
Last 16 second legs: 8/9/15/16 March
Quarter and semi-final draw: March 18
Quarter-final first leg: April 5/6
Quarter-final second leg: 12/13 April
Semi-final first leg: 26/27 April
Second leg semi-finals: 3/4 May
The final: May 28 – Gazprom Arena, St. Petersburg
