Chelsea Football Club has a storied history of managerial success, with Italian managers playing a pivotal role in shaping the club’s modern era. From Gianluca Vialli’s ground-breaking tenure to Enzo Maresca’s recent global triumphs, Italian coaches have brought tactical innovation, silverware, and a distinct flair to Stamford Bridge.
With seven Italian managers since 1998, six of whom have delivered major trophies, Chelsea’s affinity for Italian leadership is a tale of remarkable achievement.
🏆 Vialli; FA Cup, League Cup, Cup Winners Cup, Super Cup.
— CFC-Blues (@CFCBlues_com) July 14, 2025
🏅 Ranieri; Top 4 + UCL Semi-Final
🏆 Ancelotti; Premier League, FA Cup
🏆 Di Matteo; FA Cup, Champions League
🏆 Conte; Premier League, FA Cup
🏆 Sarri; Europa League
🏆 Maresca; Club World Cup + UECL
Italy 🤝🇮🇹 Chels pic.twitter.com/DrCdL2aNkW
Gianluca Vialli: The Trailblazer (1998–2000)
Gianluca Vialli, a former Juventus and Italy striker, became Chelsea’s player-manager in February 1998 after Ruud Gullit’s departure. At just 33 years and 308 days old, Vialli led Chelsea to a League Cup and European Cup Winners’ Cup double in his first season, becoming the youngest manager to win a UEFA competition—a record that stood for over a decade. He added the UEFA Super Cup in 1998 and the FA Cup in 2000, amassing five major trophies. Despite his sacking in 2000 due to player disputes, Vialli’s attacking style and charisma made him a Chelsea legend, setting the stage for future Italian managers.
Claudio Ranieri: The Foundation Builder (2000–2004)
Claudio Ranieri, dubbed the “Tinkerman” for his squad rotations, took over in 2000. Though he didn’t win trophies, Ranieri’s tenure was crucial in rebuilding Chelsea. He signed stars like Frank Lampard and nurtured John Terry, leading the club to Champions League qualification in 2002–03, which attracted Roman Abramovich’s takeover. With a £120 million transfer budget, Ranieri added players like Claude Makélélé, guiding Chelsea to a second-place Premier League finish and a Champions League semi-final in 2003–04. His groundwork paved the way for the club’s golden era.
Carlo Ancelotti: The Double Winner (2009–2011)
Carlo Ancelotti, a managerial giant from AC Milan, joined Chelsea in 2009. In his first season, he delivered the club’s first Premier League and FA Cup double, with Chelsea scoring a record-breaking 103 Premier League goals. Ancelotti also won the Community Shield, completing a treble of trophies. Despite a trophyless second season and his sacking in 2011, his 61% win rate and tactical versatility left a lasting legacy, endearing him to fans for his charismatic leadership.
Roberto Di Matteo: The Miracle Worker (2012)
Roberto Di Matteo, a former Chelsea midfielder, became caretaker manager in March 2012 after André Villas-Boas’ exit. Inheriting a struggling side, Di Matteo orchestrated a miraculous turnaround, winning the FA Cup and Chelsea’s first UEFA Champions League title, defeating Bayern Munich in a dramatic 2012 final penalty shootout. His permanent appointment followed, but a poor start to the 2012–13 season ended his tenure. With a 57% win rate and two trophies in 42 games, Di Matteo remains a Chelsea hero.
Antonio Conte: The Tactical Mastermind (2016–2018)
Antonio Conte arrived in 2016, transforming a 10th-placed Chelsea with his 3-4-3 formation. In his debut season, he won the Premier League with a club-record 30 wins, including a 13-game winning streak, earning three consecutive Manager of the Month awards—a Premier League first. Conte added an FA Cup in 2018, but a fifth-place finish led to his departure, with a £26.6 million compensation dispute. His 2.14 points-per-game average ranks among the Premier League’s best.
Maurizio Sarri: The Europa League Maestro (2018–2019)
Maurizio Sarri, known for “Sarri-ball,” joined Chelsea in 2018. Despite early criticism, he led the club to a third-place Premier League finish and the 2019 UEFA Europa League title, defeating Arsenal 4-1 in the final. Though he lost the Community Shield and League Cup final, Sarri’s 62% win rate and possession-based style added another trophy to Chelsea’s Italian legacy before he returned to Italy.
Enzo Maresca: The New Global Champion (2024–Present)
Enzo Maresca, appointed in July 2024 after leading Leicester City to the EFL Championship, brought a Pep Guardiola-inspired possession-based style to Chelsea. His impact was immediate, guiding the Blues to the 2024–25 UEFA Conference League title with a 4-1 victory over Real Betis, making Chelsea the only club to win all three major UEFA competitions.
Maresca also led Chelsea to the 2025 FIFA Club World Cup, defeating PSG 3-0 in the final to claim the club’s first global title, a historic milestone. With a fourth-place Premier League finish, securing Champions League qualification, and a 63% win rate with 29 goals in 12 games, Maresca has continued the Italian tradition of success at Chelsea.
A Legacy of Success
Chelsea’s Italian managers have delivered an impressive 14 major trophies, with only Claudio Ranieri failing to win silverware. From Vialli’s pioneering era to Maresca’s Conference League and FIFA Club World Cup triumphs, these managers have combined tactical brilliance, adaptability, and a winning mentality to elevate Chelsea’s status. Their 86% trophy-winning success rate underscores an extraordinary connection with Italian coaches. As Maresca continues to build on this legacy, Chelsea fans can celebrate a remarkable history of Italian excellence, with the promise of more silverware to come.
