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Who Are Chelsea’s Most Successful Managers of All Time?

There is an obvious dividing line when assessing Chelsea’s most successful managers, the time before Abramovich and the time after. The mercurial owner’s commercial development and investment in Chelsea turned them into one of the most feared football clubs in Europe. Chelsea have won 18 major trophies since his takeover in 2003 making the club the most successful English trophy winning team during his ownership.

The Roman Abramovich Years 2003 – Present Day

Jose Mourinho 2003-2007, 2013-2015

The defining manager of the Abramovich era, self-described “special one”. He set the tone for an era of dominance that established Chelsea as a team with a mean defence anchored by John Terry & Claude Makelele and an efficient attack with the likes of club legends Drogba, Lampard and Arjen Robben. The 2005-2006 season was a highpoint, with 18 home wins (joint PL record) and 0 defeats, becoming the first PL team to win against every team in a season. The most successful manager in Chelsea’s history, he won 8 trophies including 3 Premiership titles and a FA Cup with an overall winning percentage of 64%.

Carlo Ancelotti 2009-2011

After 8 years and 8 trophies with the Rossoneri, Carlo Ancelotti was appointed to Chelsea with much fanfare. Leading his team to their first domestic double was a triumph, beating Man United by one point and ending the PL campaign with 103 goals in year one. They were the first team in the Premier League’s history to score more than 100 goals in a season. His time was cut short in usual Abramovich fashion after two years, leaving the club with 3 trophies won and a winning percentage of 62.2%. 

Roberto Di Matteo 2012

Brought in as caretaker manager to mop up the failure of Andre Villa Boas’ half-season in charge, he will forever go down in Chelsea history as the man who led them to their first ever Champions League title. Oh, he also won the FA Cup a week prior. Unfortunately, when they were all but eliminated in the CL group stage the following year, Di Matteo faced the same axe that befell many of his predecessors, eight months after taking charge. 

Antonio Conte 2016-2018

After Mourinho failed in his second go-around at Chelsea and coming off a 10th-place finish, Antonio Conte was tasked with righting the ship. A rocky start culminated in Chelsea winning the title in his first season and an FA Cup in his second. A fifth place finish in year two was enough for Conte to go the way of many before him. For a club that prides itself on success, it wasn’t good enough. Conte left Chelsea as a fan favourite and with a winning percentage of 65.1%.

Thomas Tuchel 2021 – Present

After the mid-season dismissal of fan favourite Frank Lampard in January 2021, Tuchel was appointed with the idea to compete with Liverpool and Manchester City who have dominated the last 4 PL titles since Chelsea were champions under Antonio Conte in 2017. With similarities to Di Matteo, Tuchel won Chelsea’s second ever Champions League trophy after only a couple of months in charge. Currently sitting on top of the PL table, things are looking promising in his first full year as Tuchel looks to add to Chelsea’s bulging trophy cabinet.

Pre-Roman Abramovich Years

Glenn Hoddle 1993-1996

The 1990s was when Chelsea started to become a relevant force in British football and it started with the first of three player-manager appointments at the club. Hoddle failed to guide Chelsea beyond 11th place in the Premiership. However, he did reach a FA Cup final in his first season, semi-final of the Cup Winners Cup in his second and a FA Cup semi-final in his final year. No silverware but he set the table for the revolution that was to come.

Ruud Gullit 1996-1998

In July 1995, Gullit signed for Chelsea on a free transfer in what was at the time a truly glamorous signing for the mid-table outfit. Taking over as player-manager once Hoddle departed for the England national job, Gullit paved the way for the foreign revolution recruiting European stars including Gianfranco Zola, Roberto Di Matteo, Frank Leboeuf and Gianluca Vialli. Sexy football finally came to Chelsea FC and so did their first bit of major silverware in 26 years, an FA Cup triumph in 1997. In doing so, Gullit became the first black and non-domestic manager to win a major British trophy. Gullit was fired in 1998 despite being second in the league and still alive in cup competitions. His replacement? Player-manager Gianluca Vialli who was brought in by Gullit the year previously.

Gianluca Vialli 1998-2000

Much of Vialli’s popularity with the Chelsea fan base stems from the style and success he brought in his short tenure. Still to this day he remains the second most successful manager in terms of trophies in Chelsea’s history. Taking over from Gullit midway through the season, he won their first European trophy since 1971, the Cup Winners Cup. Adding the Super Cup, League Cup, Charity Shield and FA Cup continued the cup winning legacy that Gullit established two years prior. However, with Premiership finishes of 4th, 3rd and 5th respectively he would also lay the groundwork for Chelsea’s league success over the next twenty years.