Carlo Ancelotti can become first manager in history to reach five Champions League finals if Real Madrid can overturn 4-3 deficit against Manchester City in Wednesday's semi-final at the Santiago Bernabeu
After becoming the first coach in history to win all five of Europe's top-five leagues, Carlo Ancelotti can enter the record books again if his Real Madrid side can see off Man City.
Real's 4-0 win over Espanyol on Saturday put him alone in managerial history in leading teams from Serie A, the Premier League, Ligue 1, the Bundesliga and La Liga to league titles.
The 62-year-old is already the first man to lead four different clubs to the Champions League semi-finals, and with his side trailing Manchester City 4-3 from the first leg at the Etihad Stadium, needs only a slight change in fortunes to reach the final - which would make him the first manager to do so five times.
He was victorious in his first Champions League final with a penalty shoot-out win over Juventus at Old Trafford in 2003, but two years later was beaten on spot kicks after a stunning comeback from Liverpool in Turkey. Another two years on and he got his revenge, as Milan beat the Reds 2-1 in Athens.
Despite his close and long-term relationship with the city of Milan, perhaps his best final was saved for his first spell at the Bernabeu, where he finally helped Real Madrid to 'La Decima', their 10th Champions League trophy, an achievement they had waited 12 years to realise.
Eight years on from last lifting the European Cup, Wednesday's game in Madrid offers him the opportunity to move within 90 minutes of adding a fifth winners' medal to his collection - which would earn him another record in itself.
It marks an impressive first season back in the Spanish capital, which had started with a certain degree of apathy towards his return.
Spanish football journalist Tom Allnutt told Sky Sports: "When he arrived, it was a fairly underwhelming appointment. He wasn't unwelcome, no-one was annoyed about it, he is very popular in Madrid with the players, club and journalists but people were a little surprised.
"He's done a good job, a really good job. The main plus for him has been Vinicius Junior, his form, he's basically been transformed from what he was under Zidane. They've been a lot better defensively, he's stabilised them at the back which needed doing after they lost Sergio Ramos and Raphael Varane.
"More than anything it's the normal thing with Ancelotti, he's ridden out any storms and individual instances with players. He has that ability to make everything seem unimportant, which is a real skill and valuable for a coach of Real Madrid. It was one of Zidane's greatest strengths, to diffuse controversy, keep the players and team away from the noise.
"In part, it's because he's 62 years old, and bottom line he doesn't see it as high-pressure a job as other coaches would when they go through bad patches. He doesn't have that sense of bitterness or pressure, he's just really pleased and grateful to have another opportunity to manage Madrid. I think he thought Everton was going to be his level, so it's worked well for him and for Madrid as well."
Neville: City will fear Real's resilience on 'big week' Speaking on the Gary Neville Podcast, Gary Neville said Real's narrow 4-3 defeat in Manchester would worry opposition boss Pep Guardiola ahead of the return leg on Wednesday night.
He also raised concerns about the impact defeat could have on City's title hopes, with the Premier League top two separated by only one point with four games remaining.
He said: "They were on the canvas weren't the Real Madrid a couple of times [at Man City], but they get up and that's the thing that Pep will fear most, that however well City play however good they are in their football, however much possession they keep, they've got a dangerous, dangerous beast facing them that doesn't know how to give in and doesn't know when to stop, doesn't know how to call it a day and I think that's what's coming on Wednesday.
"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 after having lost the final last year against Chelsea disappointingly, there will be a drain on Pep Guardiola on what he wants to achieve this season, what the players want to achieve. So it's a big week. We've got big weeks coming up all the time, I know, but this is a particularly big week."