5. José Villalonga – 2 Titles
Club: Real Madrid (1956, 1957)
Villalonga made history as the first manager to win the European Cup, guiding Real Madrid to back-to-back titles. In 1956, his team defeated Reims 4–3 in a thrilling inaugural final, with Di Stéfano and Héctor Rial orchestrating the comeback. The following year, Madrid overwhelmed Fiorentina 2–0, showcasing a more controlled and disciplined performance. Villalonga’s leadership was instrumental in establishing Real Madrid’s European dominance, laying the foundation for the club’s future successes. At just 36, he remains the youngest manager to win the trophy, a testament to his tactical acumen and ability to handle pressure.
4. Bob Paisley – 3 Titles
Club: Liverpool (1977, 1978, 1981)
Paisley transformed Liverpool into a European powerhouse, blending tactical innovation with a pragmatic approach. In 1977, his team overwhelmed Borussia Mönchengladbach 3–1 in the final, driven by Kevin Keegan’s brilliance. A year later, they defended their title with a narrow 1–0 win over Club Brugge, showcasing Paisley’s ability to adapt tactically. In 1981, Liverpool defeated Real Madrid 1–0 in Paris, with Alan Kennedy’s goal securing the victory. Paisley’s ability to nurture talent and maintain Liverpool’s consistency across multiple seasons set a benchmark for managerial excellence, making him the first manager to win three European Cups.
3. Zinédine Zidane – 3 Titles
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Club: Real Madrid (2016, 2017, 2018)
Zidane’s Real Madrid achieved an unprecedented three consecutive Champions League titles, a feat unmatched in modern football. In 2016, they edged Atlético Madrid in a dramatic penalty shootout after a tense 1–1 draw. The 2017 final saw them demolish Juventus 4–1 with a masterclass of counterattacking football. In 2018, Zidane’s team triumphed 3–1 over Liverpool, with Gareth Bale scoring a sensational overhead kick. Zidane’s calm demeanor and ability to manage egos were pivotal, allowing stars like Cristiano Ronaldo to shine while maintaining team harmony. His success redefined the possibilities of sustained excellence in Europe’s toughest competition.
2. Pep Guardiola – 3 Titles
Clubs: Barcelona (2009, 2011), Manchester City (2023)
Guardiola’s Barcelona revolutionized football with their tiki-taka style, characterized by short, intricate passing and relentless pressing. In 2009, his team dismantled Manchester United 2–0, marking the arrival of a new footballing philosophy. The 2011 final was even more dominant, with Barcelona winning 3–1 against the same opponent. In 2023, Guardiola led Manchester City to their first Champions League triumph, blending his possession-based style with tactical flexibility. City’s victory, part of a historic treble, highlighted Guardiola’s evolution as a coach, able to adapt his philosophy to the demands of modern football.
1. Carlo Ancelotti – 5 Titles
Clubs: AC Milan (2003, 2007), Real Madrid (2014, 2022, 2024)
Ancelotti’s Champions League triumphs span decades, showcasing his adaptability and tactical genius. In 2003, his AC Milan team won a dramatic penalty shootout against Juventus, demonstrating defensive organization and composure under pressure. In 2007, Milan avenged their 2005 heartbreak by defeating Liverpool 2–1, with Filippo Inzaghi stealing the show. At Real Madrid, Ancelotti orchestrated the iconic “La Décima” in 2014, with Sergio Ramos’ last-minute equalizer leading to a 4–1 extra-time victory over Atlético Madrid. In 2022, his Madrid side produced a series of miraculous comebacks, culminating in a 1–0 win over Liverpool. In 2024, he claimed his fifth title, solidifying his place as the ultimate master of European football.