Managers with most wins in Chelsea history🏐

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.

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.


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.


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.