5 iconic moments from Carlo Ancelotti’s time at Real Madrid CF

With the team struggling in both LaLiga and Europe, the Real Madrid hierarchy have decided to part ways with one of their most successful managers of all time at the end of the season.

Set to leave the Santiago Bernabéu for a second time, Carlo Ancelotti is already preparing for the next chapter of his career and is close to reaching an agreement to lead the Brazil men’s national team into the 2026 FIFA World Cup. 

With that in mind, here we present to you our pick of the most iconic moments from Ancelotti’s time as manager of Los Blancos. 

5 | Winning La Decima

In what was the first UEFA Champions League final contested by two teams from the same city, neither side disappointed when it came to putting on a show. 

Ancelotti surely had his nerves jangling when Diego Godín gave Atlético Madrid the lead in the 36th minute. As the game wore on, the Madridistas grew impatient as their team struggled to find an equaliser heading into added time at the end of 90 minutes.

However, it was a towering header from skipper Sergio Ramos that helped Real Madrid take the game into extra time, where they went on to score three goals through Gareth Bale, Marcelo, and Cristiano Ronaldo to beat their bitter rivals and win their first UCL title since 2002. 

4 | Winning the 2021/22 UCL title against all odds

The 2021/22 Real Madrid side had no right to win the Champions League. And yet, Ancelotti’s men pulled off three comeback wins in the knockouts to eventually come out on top against Liverpool in the final. 

In the Round of 16, they squared off against one of Ancelotti’s former clubs, PSG. Having won the first leg at home 1-0, the Parisians started the second leg on a positive note and took a 1-0 lead before the break, leading 2-0 on aggregate. However, a Karim Benzema hattrick in the space of 17 minutes turned the tie completely and took them through to the last eight. 

Paired against Chelsea in the quarter-finals, Real Madrid won the first leg 1-3 away from home. However, with only 15 minutes left on the clock in the second leg, the Blues were leading the tie 4-3 on aggregate, having managed to come back sensationally to lead 3-0 on the night. A couple of game-changing substitutions then followed; Rodrygo levelled the tie in the 86th minute before Benzema won the tie with a 96th-minute goal in extra time. 

Then, tasked with beating arguably the best side in world football at the time in Pep Guardiola’s Manchester City, Real Madrid played one of the best knockout ties in the modern UCL format. City won a seven-goal thriller at the Etihad 4-3. In the return leg, Riyad Mahrez managed to give the visitors a two-goal lead on aggregate, having opened the scoring in the 73rd minute. 

What followed was again one from the movie scripts. Benzema, truly Real Madrid’s talisman that year, scored two goals in the 90th and 91st minutes to level the tie at 5-5. The Frenchman was once again at the forefront of his team’s success; as he completed his hattrick with a spot-kick in the 96th minute, Real Madrid secured a place in the final against Liverpool. 

The final was a cagey affair, but we didn’t get another crazy comeback as the Madridistas saw their side lift a fourteenth UCL title—a fitting end to one of Real Madrid’s most iconic runs in the tournament. 

3 | Becoming the first manager/coach to win titles in Europe’s top five leagues

Before arriving at Real Madrid, Carlo Ancelotti won the Serie A with AC Milan in 2003/04—their first since 1998/99. After Milan, Ancelotti was roped in by both Chelsea and Paris Saint-Germain, with whom he won one league title each. 

Following his brief spell with PSG and his first stint with Real Madrid, the Italian joined Bavarian giants Bayern Munich in 2016, where he won the league in his first season. 

In April 2022, “Don Carlo” became the first coach to win titles in each of Europe’s top five leagues after winning the 2021/22 LaLiga title in his second stint at Real Madrid. 

2 | Becoming the first manager/coach to win 5 UCL titles — 3 with Real Madrid

By winning the 2023/24 Champions League with Real Madrid, Ancelotti became the first coach/manager to win five UCL/European Cup titles—two clear of the second-best (Bob Paisley, Zinedine Zidane, and Pep Guardiola are tied in second with three titles each). He also became only the second head coach in history to win three UCL/European Cup titles with the same team—drawing level with Paisley, who won three European Cups with Liverpool in 1977, 1978, and 1981. 

Before his three titles with Real Madrid, Ancelotti was at the helm of one of the most dominant Milan sides in modern history, helping the Rossoneri win the 2002/03 and 2006/07 editions of the UCL. 

1 | Becoming Real Madrid’s most successful manager of all time

For a team with over 100 years of storied history, having been led by 49 full-time managers/head coaches, it was quite an achievement for Ancelotti when, in December 2024, he became the most successful manager/head coach in Real Madrid history by winning the FIFA Intercontinental Cup—his 15th trophy with the club. Ancelotti thus surpassed club legend Miguel Muñoz’s record (14). 

In his first stint with the club (2013–15), Ancelotti won one UCL title, one Copa del Rey, one UEFA Super Cup, and one FIFA Club World Cup. In this second stint, he completed two UCL–LaLiga doubles in the 2021/22 and 2023/24 seasons and also won one Copa del Rey, two Supercopas de España, two UEFA Super Cups, one FIFA Club World Cup, and one FIFA Intercontinental Cup. 

Ancelotti leaves Real Madrid with the second-best winning ratio among all who have managed the team, with a 71.55% win percentage after 341 games. Only José Mourinho has a better record (71.91%), though he was at the helm for only 178 games.