In football, a lot of clubs have a short memory when it comes to the success of their managers. Despite winning a long list of honours, managers can get replaced in an instant if the squad starts to show any sign of weakness. There are a few prestigious clubs that have seemingly gone through managers like they don’t cost anything, and Chelsea is among them.
As one of the top clubs in the English Premier League, Chelsea has a high standard when it comes to its managers. If one isn’t living up to those expectations, the next man will come in. Out of the many leaders that Chelsea has had, who ranks at the top? Here are our picks for the five best managers in Chelsea history.
There are few people in the sport of football that have a resume that’s as long as Claudio Ranieri’s. The Roman played for four clubs during his professional career and has had around two dozen different stints as manager. Some of his more notable stops include Leicester City, Inter Milan, Roma, and, of course, Chelsea. Ranieri led the club from 2000 to 2004, nearly smack dab in the middle of his job history.
Ranieri was just one shy of managing 200 matches for Chelsea, but he still ranks eighth all-time in Chelsea history in terms of matches. He also boasted a solid winning percentage at 54 percent, claiming victory in 107 matches. However, Ranieri struggled to get Chelsea over the hump as the squad didn’t win any of the major honours, but did have consistency.
After spending a 16-year career as a player with Parma, Roma, and AC Milan, Carlo Ancelotti began his managerial career in 1995 with Reggiana. After a brief period, he went to Parma for a couple of years, then found his way to Juventus and AC Milan, spending nearly a decade with the latter. Finally, Ancelotti joined Chelsea in 2009, managing the club in three different years.
Ancelotti managed just 109 matches during his Chelsea career, but had plenty of success in that time. He won 61 percent of his matches over that two-year span, which puts him third all-time in club history for managers with at least 100 matches. Ancelotti won the FA Community Shield in 2009, then followed that up in 2010 with an FA Cup title while Chelsea finished at the top of the English Premier League.
Italian native Carlo Ancelotti was one of the finest players in Serie A throughout the 1990s, spending more than a dozen years with Juventus until his retirement in 2004. Conte then managed a slew of teams during the late 2000s and throughout the 2010s, including Arezzo, Bari, and a return to Juventus. After coaching the Italian national team, Conte was hired by Chelsea to become the club’s manager.
Conte is just ahead of Ancelotti on the list of winning percentage for managers with at least 100 matches, sitting at second with 65 percent of his matches won. Conte won 69 of his 106 matches, some of which were big-time matches. In 2017, Conte’s Chelsea squad won the Premier League, and in 2018 won the FA Cup.
While most of the managers on the list were only around for a couple of years before moving on from Chelsea, Dave Sexton had one of the longer runs as the leader. Sexton spent the 1950s as a professional player, and after managing Leyton Orient for one season, became the Chelsea manager starting in 1967, holding the job for seven years.
There were some managers that held the position for many years without a positive winning percentage, but Sexton was the best of the bunch. Sexton managed 371 matches, winning 164 of them and losing 100 on the dot. Sexton was able to win the 1970 FA Cup and 1971 European Cup Winners’ Cup.
The only member of the list to hail from Portugal is also the top manager in Chelsea history: Jose Mourinho. Mourinho began his managerial career in 2000 with Benfica, then led Uniao de Leiria and Porto before getting hired by Chelsea. He had two stints as manager, with the first coming from 2004 to 2007 while the second was from 2013 to 2015.
Mourinho managed in over 320 matches and won over 200 of them. His first stint was good enough to place him at number one all-time for win percentage by a Chelsea manager while his second stint was still successful at a 59% win rate. Under Mourinho, Chelsea won the Premier League three times (2005, 2006, and 2015), three Football League Cups, the FA Community Shield, and the FA Cup in 2007.