The legendary Italian manager Carlo Ancelotti has won numerous titles across Europe’s top leagues, including the Serie A, La Liga, Bundesliga, and the Premier League. He’s the only manager in history to have won the Champions League four times, and a potential fifth title is looming.

Did we also mention he’s the first manager in history to reach the UCL semi-finals across four decades? And that he, Pep Guardiola, and Sir Alex Ferguson are the only three managers to achieve 100-plus Champions League wins?

Here, we highlight Ancelotti’s best wins to date.

Real Madrid, La Liga 2023-24

Ancelotti led Los Blancos to their 36th league victory during the 2023/24 season. It was his 6th league title and the second La Liga title of his career. But it was the style in which his team accomplished the feat — 95 points with only one defeat all season while maintaining sharpness in attack and defense despite injuries to key players. Somehow, he did not win La Liga Manager of the Season!

Real Madrid, La Liga 2021-22

Carlo Ancelotti worked wonders upon his return to Real Madrid during the 2021-22 season. By winning La Liga — previously his only missing major domestic trophy — the Italian became the first coach in history to win five major European league titles.

Don Carlo’s record of success is undeniable — the 62-year-old is still a calm, eye-brow-raised winner. Now, he’s on the brink of becoming the first-ever manager to win the Champions League four times.

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Real Madrid, Champions League, 2013-14

In his first year as the head coach of Real Madrid, Ancelotti defeated crosstown rivals Atlético Madrid 4-1 to lead Los Blancos to the Décima. It was the club’s 10th European championship and their first since 2002.

11 Best Carlo Ancelotti Wins
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Real Madrid, Copa Del Rey, 2013-14

Despite finishing third in the league after Barcelona and Atlético Madrid, Ancelotti still managed to win his first trophy. In a match against rivals Barcelona in April 2014, Real Madrid won 2-1, with Angel Di Maria and Gareth Bal scoring goals.

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AC Milan, Champions League, 2002–03

In a 2003 Champions League final against Italian heavyweights AC Milan and Juventus, Ancelotti’s side won on penalties. Ukrainian footballer Andriy Shevchenko scored the last goal to seal the deal for the Rossoneri. Milan earned its sixth European Cup.

11 Best Carlo Ancelotti Wins
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AC Milan, 2006-07 Champions League

It would be another three years before Ancelotti led his AC Milan side to another Champions League trophy. They had lost the final two years before on penalties against Liverpool in Istanbul. There was no way Ancelotti would let history repeat itself in the 2006-07 rematch between the two sides. Led by two goals from AC Milan striker Filippo “Pippo” Inzaghi, Milan beat the Reds 2-1. The win gave Ancelotti his second Champions League trophy.

11 Best Carlo Ancelotti Wins
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AC Milan, Serie A 2003–04

In the 2003-04 season, Ancelotti led the side to its 17th Scudetto. Andriy Shevchenko scored 24 goals in the season, bolstered by the arrival of Kaka and a solid defensive back-line spearheaded by Paolo Maldini.

The team set a Serie A record with 82 points in 34 games, losing twice and finishing 11 points clear of Roma.

11 Best Carlo Ancelotti Wins
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AC Milan, Copa , 2002–03

In his second season with the club, Ancelotti defeated Roma on an aggregate score of 6-3 to win the Coppa Italia Final. It was the Rossoneri’s fifth title.

11 Best Carlo Ancelotti Wins
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Chelsea, Premier League 2009-10

With an 8-0 smashing of Wigan, Ancelotti succeeded in winning the Premier League title with Chelsea in his first season with the club. The team also set a Premier League record with 103 goals in a season. Manchester United finished a mere point behind the Blues.

11 Best Carlo Ancelotti Wins
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Chelsea, FA Cup 2009-10

In 2010, Ancelotti won the double, leading Chelsea to its third FA Cup victory in four years. According to ex-Chelsea Assistant Manager Paul Clement, “Carlo Ancelotti let his Chelsea players decide their for the 2010 FA Cup final”. That’s some trust right there. The Blues beat Portsmouth 1-0 off a free-kick in the 58th minute.

Bayern Munich, Bundesliga Champions 2016-17

With a 6-0 win against Wolfsburg, Ancelotti coached Bayern Munich to its fifth consecutive title, giving the Bavarian side a total of 27 Bundesliga Championships.

11 Best Carlo Ancelotti Wins
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Paris Saint-Germain, Ligue 1 Champions 2012-13

In his second year in charge of Paris Saint-Germain, the Italian coach secured the league with two games left in the season. Unfortunately, this would be his only honor at PSG before moving to take over duties for Real Madrid.

11 Best Carlo Ancelotti Wins
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AC Milan, UEFA Super Cup 2003 & 2007

While the boss of AC Milan, Carlos Ancelotti added two Super Cup trophies: one in 2003 with a 1-0 win over and another in 2007 with a 3-1 win over Sevilla.

11 Best Carlo Ancelotti Wins
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Photo: Twitter/@footballespana_