Cristiano Ronaldo will face Manchester United for the first time since he left Old Trafford after Real Madrid were drawn against his old side in the last 16 of the Champions League.
The tie will also pit Jose Mourinho against Sir Alex Ferguson in the most mouthwatering tie of the first knock-out round of Europe's top club competition.
Ferguson said he would have to "order some good wine'' - a reference to the two managers' old tradition of sharing a glass of red after their teams' encounters.
Ferguson told the club's official website: "Well, it's the tie of the round. It's a great opportunity for our fans to see Cristiano again and also for me to meet up with Jose again - I'll need to order some good wine!''
The only other English side, Arsenal, will face last season's beaten finalists Bayern Munich while Celtic will take on Italian champions Juventus as they look for a place in the quarterfinals.
In the other matches, Barcelona will take on AC Milan, German champions Borussia Dortmund face Shakhtar Donetsk, Valencia play Paris St Germain, Porto encounter Spanish side Malaga and Galatasaray will come up against Schalke.
United's club secretary John Alexander hoped there was a lucky omen in the draw.
He told Sky Sports News: "Out of several standout ties, I think this is the one.
"It's the tie that everyone wanted to see - but that nobody wanted to see, they wanted to save it for later in the competition. When you think about the traditions of these two clubs they have both been incredibly successful, but of course the past is history. One thing going in our favor is that our one victory over Real Madrid in this competition was in the year we won the final at Wembley [in 1968] so let's hope that is a lucky omen."
It was another Ronaldo - the Brazilian striker - who took the honors when the clubs last faced each other in 2003, scoring a hat-trick at Old Trafford as Real went through 6-5 on aggregate.
United defender Rio Ferdinand played in the 2003 match against Real Madrid, as did Ryan Giggs, while Darren Fletcher was a substitute although he did not come on.
Ferdinand welcomed the draw on Twitter saying: "Oh yes, Madrid!! What a great couple a games that'll be!! @Cristiano see u soon bro!!''
Emilio Butragueno, Real Madrid's director of institutional relations, said it would be a special match for Ronaldo and the two managers.
He said on www.uefa.com: "I am sure it will be a special game for him. He's a great professional. I'm sure he's going to do his best to help us qualify. It's going to very, very special for him. It will be a thrilling experience for everyone. Manchester United are not only a great team but a great organisation known around the world.
"But we know it's going to be tough. Sir Alex Ferguson has been there over 25 years and he's a fantastic manager. He knows how to get the best out of his players and they have top players, but we are Real Madrid and we will try our best. I know the coaches have a great relationship. We are very happy with him (Mourinho) and I hope he's going to lead the team to the Champions League to make our fans feel proud of the team."
The clubs first met in the European Cup in April 1957, when Real triumphed 5-3 in the semifinal.
Cristiano Ronaldo's last match for United was in the Champions League final defeat by Barcelona, after which he moved to Madrid for a world record £80million transfer fee.
United have a slight advantage over Real in that as group winners they will get to play the second leg at home.
Arsenal and Celtic, who were group runners-up, will both play their second legs away.
Arsene Wenger's Gunners last met Bayern Munich at the same stage in 2005, with the German side progressing 3-2 on aggregate.
Celtic boss Neil Lennon called his side's draw against Juventus "a beauty" but very tough.
Lennon told Sky Sports News: "Well in terms of glamour it's a beauty. Juventus are one of the great traditional European teams. They're current Italian champions and finished the group stage very strongly.
"So in terms of glamour it's great, in terms of qualification it is going to be very tough, but it could have been any of the other teams and it would have been just as tough. We will take it as it comes, we're looking forward to the games now and I'm sure our supporters will be as well.
"We believe over two games anything is possible. Juventus are littered with world-class stars and have been very consistent over the last 18 months and have got a great winning mentality, but so have we.
"It's very exciting for me as a young manager to be in this position, to sit there and watch the draw today. It's come very early in my managerial career but I'll never forget today. Now we can prepare for the challenge of facing Juventus."
Champions League Round of 16 draw:
Galatasaray vs Schalke 04
Celtic vs Juventus
Arsenal vs Bayern Munich
Shakhtar Donetsk vs Borussia Dortmund
AC Milan vs Barcelona
Real Madrid vs Man Utd
Valencia vs PSG
FC Porto vs Malaga
First legs to be played 12/13/19/20th February, 2013
Second legs to be played 5/6/12/13th March, 2013
