The old saying that to win the Champions League you have to beat the best will be little comfort to José Mourinho after Thursday's draw.
Having successfully navigated the group of death to reach the knockout stages, Mourinho's Real was plucked from the tombola and matched with Sir Alex Ferguson's Manchester United. Another trip to the north of England where the two experienced managers will renew a fascinating rivalry.
John Alexander, Manchester United's secretary, summed up the feeling in the two camps perfectly after the draw in Nyon: "It's the game that everybody wanted to see but nobody wanted to see. If history has anything in our favour it's that our one victory against them in this competition was in the year that we won the final in Wembley."
This European clasico has produced some memorable matches: Ronaldo's hat-trick at Old Trafford in 2002-03 particularly, which also featured a star turn from Real-bound David Beckham, who started on the bench as his relationship with Ferguson disintegrated.
Or the 1957 semifinals, which ended 5-3 on aggregate to Real with Alfredo di Stefano and Bobby Charlton both on the score sheet.
"This tie is going to be difficult," noted Real director Emilio Butragueno. "The Champions League is the most prestigious club competition in the world. Playing against Manchester United is going to be another factor for our players. They will think 'I want to show what I'm made of' [against such lauded opponents]. It's very important for us to get our injured players back but the first leg is two months away so I hope we will be at our best and I hope we will be on form. It's unpredictable."
Hopefully both sides will be able to put out their strongest teams, which for Real is very fixed but for United remains a large question mark. Shinji Kagawa is set to return for Ferguson's team over the festive period, which will give the wily Scot a chance to revisit the Japanese star's promising partnership with Tom Cleverly.
But then how will he crowbar both Robin van Persie and Wayne Rooney into the side with the Asian Player of the Year back? It's a conundrum many managers would be happy to have. Ferguson has favored a 4-4-1-1 in the big matches this season with Van Persie's place at its head assured. It will be interesting to see how he lines up at Old Trafford in two months' time.
Midfield is arguably Ferguson's problem area. The aging Paul Scholes and Ryan Giggs lack the legs to give Real the runaround, Michael Carrick is too lightweight to contain Real and United's wide players are inconsistent. Whoever plays up front will have to be prepared to drop back into midfield, one of Rooney's strong points.
Like Mourinho at Real, Ferguson has had problems at the back with Nemanja Vidic out injured for several weeks and Rio Ferdinand's back problems keeping him on the sidelines. Ferguson will need his Serbian captain at his best for the Real tie.
Another area Ferguson has yet to settle is goalkeeper, where Anders Lindegaard and David de Gea are jostling for the No. 1 spot. That is one area where Real has no such problem.
Mourinho's side has also been beset by injuries of late but he should have a full complement of first team players to pick from in February. Karim Benzema will be vital with ability to pull defenders out of position, but the form of Cristiano Ronaldo could be the decisive factor.
The former United player has the ability to turn a game on his own, as he did many times at Old Trafford. The Portuguese winger will need to ensure that the occasion doesn't get the better of him and that whatever reception he might receive does not affect him. There is little less effective than a frustrated Ronaldo playing for himself.
It promises to be an exciting tie, although it is probably one both sides would rather be playing in May.