Beating Bayern Munich is not an easy task, but if there is any man who knows how to do it, it’s Carlo Ancelotti.
He won four of those games and drew the other two, although the Bayern that Madrid face on Wednesday night is a different proposition.
Between 2002 and 2007 Milan won twice in Germany against Bayern in the Champions League and drew once.
At home they have the same record, including a 4-1 thrashing of the Germans at the San Siro in the second leg of the 2006 last 16.
The most recent clash was in April 2007, when veteran stars Clarence Seedorf and Filippo Inzaghi found the net.
Who will win?
Only Philipp Lahm remains from the Bayern squad that was selected that day.
However, Jupp Heynckes turned an impressive outfit into a ruthless killing machine, and this season Pep Guardiola has added still more fizz into the mixture at the Allianz Arena.
Real Madrid supporters will be anxious to beat Bayern for that—Guardiola is despised in Madrid thanks to the rivalry between Los Blancos and Barcelona.
But achieving La Decima, their tenth top European title, is even more important than getting one over Guardiola.
Ancelotti has had trouble in the bigger games this season, losing to Barcelona twice and Atletico Madrid once.
But in the Copa del Rey final, his team overcame Barcelona, and that was without star man Cristiano Ronaldo.
He is set to return from injury to face the Germans, and along with Karim Benzema and Gareth Bale, will be key.
Ancelotti said, at his pre-match press conference, as per ESPN journalist Dermot Corrigan: "I have a lot of respect for Guardiola. [But] I dont believe the coaches will decide this semi, the players will decide it.”
While you could easily believe that, because an individual moment of skill from Bale, Ronaldo, Franck Ribery, Arjen Robben or Mario Gotze can win a match, it does not do justice to what will be a fascinating battle on the sidelines.
How Ancelotti sets up his team is going to play a huge role in the proceedings.
Madrid like to play attacking, proud football. But they may be better served by trying to hit possession-loving Bayern Munich on the counter.
Sergio Ramos and Pepe, protected by Xabi Alonso, are strong enough players to turn the penalty area into a fortress, and the pace of Madrid on the break is unrivaled.
Angel Di Maria has been superb this season and he, along with the aforementioned front trio, can be lightning quick with their counter-attacks.
Ancelotti continued, per Corrigan: "Bayern as 'Bestia negra' [is] not a mental thing for me, I have a good record against Bayern and confidence in the players I have."
"Bestia negra" stands for "black beast," a name that fans and journalists in Madrid have labelled Bayern, after a run of key defeats by them.
The last clash between Bayern and Real saw the latter knocked out in the 2012 semi-finals, on penalties.
Bayern Chairman Karl-Heinz Rummenigge believes that the Germans need to live up to their name.
He said, per AFP (via NST.com): "We’re known as 'la bestia negra' down there and we need to show them 'la bestia negra' is back. We need to score at least one goal. That’s what we learnt from Dortmund’s meetings with Real Madrid.”
Without a doubt, Bayern are the team to beat this season.
But given his impressive record against them and a history of success, Ancelotti will not be losing too much sleep about it.