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Chelsea are one of the top clubs in England and Europe. They have carved out a niche for themselves, especially since their takeover by Roman Abramovich in the early 2000s.
The Blues are one of only three clubs to have won at least five Premier League titles. Last season, they joined Manchester United (3), Liverpool (6) and Nottingham Forest (2) as the only English clubs to triumph multiple times in the UEFA Champions League.
Regulars in the English top flight since 1989-90, the Blues have won eight FA Cups, five League Cups and two Europa League titles as well. They recently added the FIFA Club World Cup to their burgeoning trophy cabinet.
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Considering their rich history and pedigree, many fine players and managers have graced the club, winning games and titles galore. On that note, here's a look at the five Chelsea managers with the most wins in the club's history:
#5 Tommy Docherty - 143
Tommy Docherty spent five and a half seasons at Stamford Bridge during a reign that is often described as 'never dull and predictable'.
He took over from Ted Drake (more on him later) - the Blues' only league-winning manager - in 1961. Docherty inherited a young team (average age 21 years) and instantly returned them to the top flight. He introduced the club's iconic blue-white strip, which the Blues still use to this day.
In terms of trophies, the late Scotsman only delivered one League Cup (1964-65) title at Stamford Bridge. However, he was renowned for his modern yet rebellious outlook, inbibing the best practices from the top clubs of his era.
Docherty's ouster in 1967 for off-the-field incidents prompted a spoof obituary in The Times, mourning the 'death of Chelsea FC', such was his aura. He eventually passed away in December 2020 at the age of 92.
#4 Ted Drake - 155
Ted Drake has a special pride of place in the Blues' history, leading the club to their first English First Division title in 1954-55. Drake, who amassed 42 strikes in Arsenal's league-winning campaign in 1934-35, became the first man to win the English top flight title as both player and manager.
The former England and Arsenal legend arrived at Stamford Bridge from Reading in 1952 and set about introducing young players to an aging squad. However, his league title triumph in 1955 would be his only piece of silverware at the Blues during his near decade-long stint at the club.
The team's fortunes steadily plummeted, and the Blues were hurtling towards relegation when Drake was shown the door in 1961. He expired in May 1995 at the age of 82.
#3 Dave Sexton - 165
Dave Sexton is another legendary manager to have assumed the reins at Stamford Bridge.
The late Englishman had a memorable six-season stint at the club between 1967 and 1974, winning the Blues' first of eight FA Cups in 1969-70. Their win over Leeds in the final remains one of the most-watched football matches in British television history. The Blues won the replay 2-1 after the first meeting ended 2-2.
The Cup Winners' Cup followed the next campaign, Chelsea's first European title. In the final against Real Madrid, Sexton demonstrated his tactical nous and managerial pedigree.
However, things soon turned south, and Sexton was relieved of his duties in October 1974 after a breakdown in relations between the manager and the club. Nevertheless, he is fondly remembered as one of the club's greatest-ever managers. He passed away in November 2012 at the age of 82.
#2 Jose Mourinho - 204
Jose Mourinho is one of the most successful Blues managers, especially in the Roman Abramovich era.
Calling himself 'The Special One' when he first arrived on English shores in 2004, Mourinho walked the talk. He helped the Blues win their first league title in five decades, conceding a record-low 15 goals all season and losing just once. Another title followed the following season before Mourinho delivered a third nine years later, during his second stint at the club.
The Portuguese also added one FA Cup, three League Cups and one English Super Cup before leaving Stamford Bridge for the second time in December 2015.
#1 David Calderhead - 385
David Calderhead holds the distinction of being Chelsea's longest-serving manager, managing the club for 26 long years (1907-1933).
Described as a 'man of a few words but homespun wisdom aplenty', the late Scot took Chelsea to their first FA Cup final in 1915. Though he won no silverware at the Pensioners (as Chelsea were nicknamed back then), he brought them back to the top flight twice (1912 and 1930) - either side of the First World War.
He passed away in 1978 at the age of 73, having won the FA Cup with Notts County as a player in 1894.
