With the club struggling to fight both in La Liga and in 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 2024/25 La Liga seasons, with the 65-year-old Italian close to reaching an agreement with the Brazilian men’s national team to lead the side into the 2026 FIFA World Cup.
With that in mind, in this article, we’ll take a look at the top five iconic moments from Carlo Ancelotti’s stint as the Real Madrid manager.
5 | Winning La Decima
In the first Champions League final that would be contested by two teams from the same city, neither team disappointed to put 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 the team failed to find an equaliser with the team heading into added time at the end of the 90 minutes. However, it was a towering header from then skipper Sergio Ramos that helped Real take the match into extra time.
They would later go on to score three goals in extra-time through Gareth Bale, Marcelo and a Cristiano Ronaldo spot-kick, to beat their bitter rivals and win their first UCL title since 2002, thanks to Carlo Ancelotti.
4 | Winning the 2021/22 UCL title against all odds
The 2021/22 Real Madrid side had no right to win the Champions League, however, Ancelotti’s team pulled off three comeback wins in the knockout stages to eventually come out on top against Liverpool in the final.
In the Round of 16, Real squared off against Ancelotti’s former club PSG, with the Parisians winning the first leg at home 1-0. PSG started the second leg on a positive note, taking a 1-0 lead before the break, leading 2-0 on aggregate. However, a Karim Benzema hat-trick in the space of 17 minutes turned the tie completely and took them through to the last eight.
Paired up against Chelsea in the quarter-finals, the Galacticos won the first leg 1-3 away from home. However, with only 15 minutes left on the clock, German striker Timo Werner gave the visitors an unlikely 3-0 lead at the Santiago Bernabéu and a 4-3 lead on aggregate. A couple of game-changing substitutions resulted in Rodrygo levelling the tie in the 86th minute before Karim Benzema won the tie for Madrid with a 96th minute goal in extra time.
Tasked to see off arguably the best side in world football at the time in Pep Guardiola’s Manchester City, the two giants of European football played one of the best knockouts ties in the modern UCL format with City winning a seven-goal thriller at the Etihad Stadium 4-3. In the return leg, Riyad Mahrez gave the visitors a two-goal lead on aggregate after opening the scoring in the 73rd minute.
What followed was again one from the movie scripts. Real Madrid’s talisman that year Karim Benzema scored two goals in the 90th and then in the 91st minute to level the tie at 5-5 after the full-time whistle at the Santiago Bernabéu. Benzema once again was at the forefront of Madrid’s success when he completed his hat-trick with a spot-kick in the 96th minute to win the tie and book a place in the final against Liverpool.
The final was a cagey affair but didn’t need another crazy comeback as the Madridistas lifted their fourteenth UCL title, largely helped by one of the club’s most iconic runs in the tournament.
3 | Becoming the first manager/coach to win titles in Europe’s top five leagues
Besides Real Madrid, Carlo Ancelotti also won league titles with AC Milan (2003/04) – their first since 1998/99. After Milan, Ancelotti was roped in by both Chelsea and Paris Saint-Germain where he won one league title each.
Following his brief spell with PSG, the Italian joined Bavarian giants Bayern Munich for the 2016/17, where he won the title in his first season.
In April 2022, Don Carlo became the first coach to win titles in Europe’s top 5 leagues after winning the 2021/22 La Liga title in his second stint at the club.
2 | Becoming the first manager/coach to win 5 UCL titles — 3 with Real Madrid
Following Real Madrid’s 2023/24 UCL triumph, Italian head coach Carlo Ancelotti became the first coach/manager to win five UCL titles, two clear of the second-best with three titles. Moreover, Ancelotti also became only the second head coach in history to win three UCL/European Cup titles with the same team – drawing level with Bob 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 AC Milan sides in modern history, helping the club win the 2002/03 and 2006/07 editions of the competition.
1 | Becoming Real Madrid’s most successful manager of all time
For a club with over 100 years of history and one that has had 49 full-time managers/head coaches, in December 2024, Carlo Ancelotti became the most successful manager/head coach in the club’s history. Following his FIFA Intercontinental Cup triumph, which was his 15th title with the club, Ancelotti surpassed club legend Miguel Muñoz (14) as the most successful manager in the club’s history.
In his first stint with the club from 2013-2015, the Italian head coach won one UCL title, one Copa del Rey, one UEFA Super Cup and one FIFA Club World Cup. In this second stint, Ancelotti completed two UCL-La Liga doubles in the 2021/22 and 2023/24 seasons. He also won one Copa del Rey, two Supercopa de España, two UEFA Super Cups, one FIFA Club World Cup and one FIFA Intercontinental Cup.
Moreover, he has the second-best winning ratio among all Real Madrid managers/head coaches with a 71.55 win ratio in 341 games, only José Mourinho has a better record (71.91), however, the Portuguese was at the helm for only 178 games.
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