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Ranking Chelsea’s top 5 managers of all time

Chelsea have had production line of great managers over the years
Chelsea have had production line of great managers over the years
Modified 23 Mar 2021
Top 5 / Top 10

Chelsea and managers have not exactly been a match made in heaven in the Roman Abramovich era that begun in 2003. In almost 18 years, the Chelsea manager’s job has changed hands 17 times – cementing its status as a poisoned chalice in every sense of the word.

However, despite his tendency to wield the axe in order to see his investment thrive, what can’t be disputed is the glory Abramovich has brought to the club. The Russian transformed Chelsea, who had a patch of success in the 60s and early 70s, from a club backed by the crème de la crème of London, to one of the most successful football organisations in the world.

18 trophies have followed, with Chelsea being the first and only London club so far to have lifted the Champions League. Success has a tendency to attract the world’s best players, with Arjen Robben, Didier Drogba, Petr Cech, Ashley Cole, Michael Ballack, Nicolas Anelka, John Obi Mikel, Claude Makelele, Juan Mata, Eden Hazard and Diego Costa just some of the big names purchased on the Russian’s watch.

Of course, it takes a manager to call the shots, with Chelsea having also attracted the biggest names in management over the years. So, who amongst Chelsea’s Christmas list of managers are the standouts? You’re about to find out as we get to ranking Chelsea’s top 5 managers of all time.

#5 Ted Drake

Chelsea Team Talk
Chelsea Team Talk

Ted Drake was in the Chelsea hot seat from 1952 to 1961, way before Abramovich’s time, and is relatively unknown amongst today’s supporters, but his achievements, along with the sweeping changes he ushered in, make him an important part of the club’s history.Aside froms delivering the double in 1955, which made him the only Blues boss to win the league in the 20th century, Drake is also credited for introducing the now-iconic lion to their crest.

Other changes brought about by Drake include the introduction of scouting reports as well as a ballwork-based training regime – which was a revolutionary practice at the time. The Englishman also preferred raw talent over big signings, and preferred to recruit players with potential from the lower leagues.

Drake also gave debuts to an exciting crop of young players, which included Jimmy Greaves – who is the highest ever scorer in the English top flight, Peter Brabrook and Bobby Tambling. The former manager’s changes became integral to Chelsea’s identity, making him a vital part of their DNA.

#4 Gianluca Vialli

Gianluca Vialli, Dennis Wise
Gianluca Vialli, Dennis Wise

Few individuals have been an immense success at a club as a player, only to surpass those achievements at that very club as manager. Legendary Italian striker Gianluca Vialli is part of that elite bunch. What makes Vialli’s case even more incredible is that a lot of those achievements came during his time as player-manager of the Blues.

After scoring goals for fun at Chelsea as a player, Vialli continued that winning form as a manager – replacing Ruud Gullit, the man who signed him – while still turning out for the club in 1998. The Italian won three trophies in his debut season as Blues boss in the form of the League Cup, UEFA Cup Winners’ Cup and the UEFA Super Cup – with the last one coming after a famous 1-0 victory over Champions League holders Real Madrid in the final.

Chelsea also finished third in the league during Vialli’s first season at the helm, their highest league finish since 1970 and the closest they came to winning the title since their triumph in 1955.

The Italian brought Champions League football to Stamford Bridge for the first time ever in his second season, and memorably defeated Barcelona 3-1 in the first leg of the quarterfinals, only to be beaten 5-1 in the return leg.


Despite a lukewarm second season, Chelsea still managed to win the FA Cup under the Italian’s stewardship, increasing his stock at Stamford Bridge. Vialli’s third and final season as Chelsea boss began on a high with a Charity Shield victory over Manchester United, but the club failed to capitalise on that promising start.

That, combined with Vialli’s strained relationship with his players, led to his departure in 2000. Vialli left Chelsea as their most successful manager up to that point, and still holds the distinction of being the Blues’ most successful boss of the pre-Abramovich era, making him a key part of the club’s history.

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Published 23 Mar 2021, 02:03 IST
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