If Real Madrid can beat Man City, Carlo Ancelotti will become the first coach in history to win all five of Europe's top-five leagues.
He is the only manager in history to lead teams from all over the world to league titles.
The 62-year-old is already the first man to lead four different clubs to the final of the competition, and with his side trailing Manchester City 4-3 from the first leg, needs only a slight change of fortune to reach the final.
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He won the first of his two European titles in 2003 with a penalty shoot-out win over Juventus, but two years later he was beaten on spot kicks after a stunning comeback from Istanbul. He got revenge as Milan beat the Reds in Athens.
Despite his close relationship with the city of Milan, perhaps his best final was saved for his first spell at the Bernabeu, where he helped Real Madrid to their 10th trophy, an achievement they had waited 12 years for.
He can move within 90 minutes of adding a fifth winners medal to his collection if he wins the European Cup game in Madrid on Wednesday.
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It marks an impressive first season in the Spanish capital, which had started with a certain degree of apathy towards his return.
Tom Allnutt, a Spanish football journalist, told Sky Sports that when he arrived, it was a fairly lackluster appointment. He is very popular in Madrid with the players, club and journalists but people were a little surprised.
He has done a good job. Vinicius Junior has been the main plus for him, he has been transformed from what he was before. They have been a lot better defensively since they lost Raphael Varane and Sergio Ramos.
More than anything, it is the norm for him to ride out storms and individual instances with players. He has the ability to make things seem unimportant, which is a real skill for a Real Madrid coach. It was one of the greatest strengths of the team, to keep the players away from the noise.
He doesn't see it as high-pressure a job as other coaches would when they go through bad patches. He doesn't have a sense of pressure or bitterness, he is really happy and grateful to have another chance to manage Madrid. I think it worked well for him and for Madrid because he thoughtEverton was going to be his level.
Manchester City could have Kyle Walker back in action for Wednesday’s Champions League semi-final second leg at Real Madrid. Defender Walker, who has been absent for the last five matches while recovering from an ankle issue, has trained and was due to travel with the squad to Spain, with a late decision to be made.
John Stones remains sidelined after coming off in the first half of the 4-3 first-leg victory last week, while Joao Cancelo, suspended for that match, is available.
Gary Neville said that the narrow 4-3 defeat in Manchester by Real would worry the opposition boss.
With only four games left in the season, the top two in the league are separated by only one point, and the impact of the defeat could have on City's title hopes.
He said that they were on the canvas a couple of times at Man City, but they got up and played good football.
The reason I mentioned this game is that I think it will have a huge impact on the City mentality for the rest of the season, because if they do go out of Europe on Wednesday, there will be a drain onPep. It is a big week. We have big weeks coming up all the time, but this is a particularly big week.
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