Carlo Ancelotti is one of the most decorated coaches in football history having won titles across Europe. He is the only coach to have won the league in all five of the continent’s major leagues, and one of three coaches to have won the Champions League three times.
As Ancelotti’s Real Madrid prepares to face Liverpool in the Champions League final in Paris, let’s take a look at his record in major cup finals throughout his career.
1999 Intertoto Cup – Juventus 4 – 2 Rennes (total)
Having made a name for himself in Reggiana and Parma, Ancelotti took over Juventus from Marcelo Lippi and immediately won the title in his first season. Juventus was one of the three winners of the Intertoto Cup, beating Rennes 4-2 on aggregate.
The first leg, which was held in Cesena, won 2-0 and Bebo Inzaghi scored both goals – a prelude to the partnership with Ancelotti that will bring much success later. Rennes took an early lead in the second leg in France but unexpected goalscorers Antonio Conte and Gianluca Zambrotta secured a draw despite a late equalizer last night.
UEFA Champions League – 2003 – AC Milan 0 (3) -0 (2) Juventus
After his dismissal by Juventus, Ancelotti returned to Milan, where he spent most of his career. A quiet first season was followed by an impressive second season in 2002-03 in which Milan secured the Champions League and Coppa Italia while finishing third in the league.
The highlight was the victory over his old team Juventus in the Champions League final in Manchester. A benign game with few chances was decided by penalties after Dida, who had been backed by Ancelotti amid criticism the previous season, made three saves in a penalty shootout. Milan became the European champion for the first time since 1994.
Italian Cup – 2003 – Milan 6-3 Roma (total of two matches).
Just three days after their continental win, Milan secured their second title of the season thanks to a 2-2 draw in the second leg at the San Siro against Roma. Ancelotti’s side did most of the work in the first leg, scoring four goals in the second half to seal a 4-1 win away to home in the capital.
Serginho scored twice in the first leg, along with Shevchenko and Ambrosini’s goals, while Rivaldo and Inzaghi scored in the second leg. Francesco Totti scored all three goals for Roma.
Intercontinental Cup – 2003 – Milan 1 (1) – 1 (3) Boca Juniors
The predecessor of the Club World Cup was the site of Carlo Ancelotti’s first defeat in the final. Ancelotti’s team played in Japan and lost to Boca Juniors led by Carlos Bianchi on penalties in the decider.
Thomason gave Milan an early lead, but Donnett equalized Boca soon after. The penalty shootout from Milan was so bad with both Pirlo, Seedorf and Costacurta failing to score, allowing Boca to take the trophy.
UEFA Champions League – 2005 – AC Milan 3 (2) – 3 (3) Liverpool
Ancelotti suffered his second defeat in the final on that infamous night in Istanbul. After leading 3-0 in the first half through Crespo’s double and Maldini’s goal in the first minute, Milan collapsed in the second, conceding three goals in six minutes to send the match into overtime.
🔥 Undoubtedly one of the greatest #UCLfinal all times.
🔴 Liverpool 2005 #UCL A victory dubbed “The Miracle of Istanbul”;
Half time: AC Milan 3-0 Liverpool
Full-time: AC Milan 3-3 Liverpool
Liverpool won 3-2 on penalties after extra time.#LFC|# Liverpool|#UCL pic.twitter.com/84PeaAOxdA
– #ChampionsLeague (@alimo_philip) May 27 2022
Two years after the successful penalty kick against Juventus, the tables turned on Ancelotti’s side as Liverpool goalkeeper Jerzy Dudek saved two goals and Serginho hit the net to give the English side an unlikely best win.
UEFA Champions League – 2007 – Milan 2 – 1 Liverpool
The Rossoneri avenged their defeat in Istanbul two years later, as they beat the Reds in Athens to win their seventh Champions League title. Just as in Ancelotti’s first final, it was Bebo Inzaghi’s double that got the job done.
On this day: In 2007, Milan won their seventh Champions League title after beating Liverpool 2-1 in Athens.
Revenge of Istanbul. pic.twitter.com/UUbyKM2gHB
– Squawka (Squawka) May 23, 2020
It was a professional and efficient performance under pressure, something that has since become synonymous with Ancelotti’s team.
FIFA Club World Cup – 2007 – AC Milan 4-2 Boca Juniors
A few months after his success in the Champions League, Milan completed another revenge by defeating Boca Juniors for the FIFA Club World Cup after four years of denying the Argentine team the title.
Inzaghi and Palacio exchanged blows in the first half, but three goals in twenty minutes in the second half ensured the Italian team’s victory, despite Ledesma’s late consolation.
2010 FA Cup – Chelsea 1-0 Portsmouth
After spending 14 years as a coach in Italy, Ancelotti moved to newly wealthy Chelsea at the start of the 2009-10 season and brought with him the winning touch. The retirees won the Premier League and FA Cup double in the Italian first season at Stamford Bridge.
Didier Drogba + Wembley Stadium = goals 💥#HeadsUpFACup @Chelsea Football Club pic.twitter.com/42VTtIpT9j
Emirates Cup 27 July 2020
A single goal scored by Wembley himself, Didier Drogba, was enough to see Chelsea win the oldest competition in world football. They beat Portsmouth, who became the first team since 1997 to reach the cup final and were relegated from the English Premier League in the same season.
King’s Cup – 2014 – Real Madrid 2-1 Barcelona
Ancelotti took over from Jose Mourinho at the Santiago Bernabeu at the start of the 2013-14 season, and like his previous appointments, success didn’t take long. Real Madrid beat eternal rivals Barcelona in a dramatic final at Mestalla to win only the King’s Cup for the second time in 20 years, and their last domestic cup win to date.
On This Day: In 2014, Gareth Bale produced *this* great off the field and turned Marc Bartra to score the winning goal in the Copa del Rey final.
His first 13 titles with Real Madrid. 💨 pic.twitter.com/utLiTUMQX0
– Squawka (Squawka) April 16, 2020
Angel Di Maria gave Los Blancos an early lead before Marc Bartara equalized for Barcelona in the second half. Five minutes before the end of time, Gareth Bale turned on the rear flares to run from inside the attacking break and bypassed Jose Pinto for a creative winner.
UEFA Champions League – 2014 – Real Madrid 4-1 Atletico Madrid (after the match).
Real Madrid broke the tenth cup curse thanks to Ancelotti when they beat local rivals Atlético in the 2014 Champions League final in Lisbon. Diego Godin’s first-half goal looked like it would give Atlético their first-ever European Championship, but a belated comeback broke Los Colchoneros’ hearts.
🗣️ “I said to myself, ‘It can’t end like this. “
2⃣ Sergio Ramos added to his crucial goals against Bayern in the semi-finals, forcing extra time into a last-gasp draw in Lisbon against rivals Atlético. “La Décima” will become reality@Sergio Ramos | Tweet embed | #UCL pic.twitter.com/sGC7BMlNgT
UEFA Champions League March 24, 2021
Sergio Ramos equalized in the 94th minute to send the match into extra time before three goals in the last ten minutes of 120 minutes Bale, Marcelo and Ronaldo handed the trophy to Madrid.
FIFA Club World Cup 2014 – Real Madrid 2-0 San Lorenzo
Carlo Ancelotti’s team became the world champion when they beat Argentina’s San Lorenzo in Marrakesh. It was a routine win with the Champions League final champions a few months ago, Ramos and Bale, as they scored goals to secure the trophy.
This was Ancelotti’s last major final as his time in Madrid was followed by somewhat disappointing spells with Bayern Munich, Napoli and Everton. Returning to the Bernabeu this season, can he lead Real Madrid to win the 14th Champions League title?