We examine the finest managers to ever take the helm at Stamford Bridge and reveal the greatest Blues boss ever.
While many of England’s top sides have built their success on stability in the dugout, Chelsea’s success has come from a relentless high standard for their bosses.
Roman Abramovich was known for his impatient approach with managers, but his predecessor Ken Bates went through 10 bosses during his 20-year reign, and six different men have taken charge of the team in the current owners’ three-year tenure.
In the 120 years since the club was founded, just six managers have spent more than four seasons in charge and there’s little doubt that the Chelsea job is one of the most demanding in English football, but the club have enjoyed a huge amount of success over the past two decades and are regularly among the title favourites in the Premier League betting.
Here is our list of the 10 best managers the club has ever seen, and make sure to explore our ranking of the best ever Premier League managers.
10. Antonio Conte
Antonio Conte’s spell at Stamford Bridge had a sour ending and he didn’t endear himself to the Blues’ support when he returned to manage Tottenham. However, his arrival in 2016 galvanised a squad fresh from the worst title defence in Premier League history.
After a mixed start, Conte switched to a back-three and led his team to win every league game in October, November and December. He brought a mini-tactical revolution to the English game in the year Pep Guardiola arrived, while temporarily turning Victor Moses into an elite wing-back.
9. Claudio Ranieri
Claudio Ranieri has certainly enjoyed bigger triumphs elsewhere, but his role in guiding a pre-Abramovich Chelsea into the Champions League in 2002/03 was vital.
The Blues were facing huge financial pressures, but Ranieri steadied the ship. In the first season of their new era, the Italian led them to second and a run to the Champions League semi-finals.
8. Roberto Di Matteo
As Chelsea desperately chased the Champions League, they turned to a World Cup-winning Brazilian before appointing a man who has now won the trophy seven times. Where they failed, former MK Dons and West Brom coach Roberto Di Matteo succeeded.
Di Matteo was enlisted as Andre-Villas Boas’ assistant in 2011. Given the churn of managers at that time, they tended to partner them with a familiar name as an assistant.
Di Matteo stepped in to see out an unravelling 2011/12 season as caretaker, finishing it by lifting two trophies. He only lasted six months after that incredible night in Munich, but he holds a unique place in Chelsea history as a player and a manager.
7. Dave Sexton
Dave Sexton was the first man to deliver a European trophy to Stamford Bridge, as he led the Blues to a Cup Winners’ Cup success over Real Madrid in 1971.
Sexton also secured Chelsea’s first FA Cup win in 1970, beating Don Revie’s Leeds United in a replay in the final.
Issues with the players led to him breaking up that squad before the club was relegated in 1975, but he achieved enough to earn a spot on this list.
6. Tommy Docherty
Sexton may have taken Chelsea over the line in the ‘70s, but he was building on the great work of Tommy Docherty.
The Scotsman took charge as the club was on the way to relegation in the 1961/62 campaign. However, he rebuilt the side and immediately bounced back with promotion.
Docherty put together a core of Chelsea legends, including Peter Osgood, Peter Bonetti, and Bobby Tambling, on his way to winning the League Cup in 1967.
5. Gianluca Vialli
Given Chelsea’s glittering last 20 years, it’s remarkable that Gianluca Vialli won more between 1998 and 2000 than all but one other Chelsea boss.
He built on the good work undertaken by Glenn Hoddle and Ruud Gullit before him to win five different competitions: the 1998 League Cup and UEFA Cup Winners’ Cup, the 1999 UEFA Super Cup and the 2000 FA Cup and Community Shield.
Vialli also guided the Blues to third place in the Premier League in 1999/2000, which was their best league finish since 1970.
4. Carlo Ancelotti
Carlo Ancelotti’s departure in 2011 remains one of the harshest sackings in Chelsea’s history.
Few Blues bosses have gone on to sustained success after leaving Stamford Bridge, but Ancelotti has won 19 trophies since being dismissed in a corridor of Goodison Park minutes after the 2011/12 campaign ended.
His first season in England ended on a much brighter note, leading the Blues to their first-ever league and FA Cup double. He was also the first Chelsea manager to deliver the style of football Abramovich wanted, as the club broke the record for Premier League goals in a season.
3. Thomas Tuchel
The new England boss produced one of the finest coaching displays in recent years when he arrived at Stamford Bridge. Thomas Tuchel transformed a side which looked inexperienced and flimsy under Frank Lampard into the finest defence in Europe.
Tuchel’s Blues routinely schooled Guardiola’s Man City, including in the 2021 Champions League final. The German won three trophies in total, also leading them to the final of the FA Cup and EFL Cup. Ownership issues and injuries hampered the rest of his spell, but the club’s recent struggles put his final months in charge into perspective.
2. Ted Drake
Ted Drake’s influence on Chelsea remains to this day, having pushed to put a lion on the club crest.
He took charge of the club in 1952 and he guided them to the Premier League title in 1955 – 50 years after the club’s formation – and became the first man to lift the trophy as both a player and manager.
His place in Chelsea folklore only grew after his departure, as the club waited another 50 years to return to the summit of the English game.
1. Jose Mourinho
In one of the most famous – and often misquoted – lines in the history of English football, Jose Mourinho arrived claiming he was, “a special one”. It’s fair to say he delivered.
The Portuguese came to England having just won the Champions league with Porto, and enjoyed immediate success at Stamford Bridge, winning the Premier League in each of his first two seasons in charge. Mourinho also won the League Cup twice and the FA Cup once during a hugely successful three-year spell at the club.
Mourinho returned in 2013 and led the Blues back to the top once more with another league title and a third League Cup triumph, establishing himself as one of English football’s most decorated and iconic figures.
