Ranking Chelsea’s top 5 managers of all time

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

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

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.

#3 Roberto Di Matteo

FC Barcelona v Chelsea FC - UEFA Champions League Semi Final

The Italian’s time in the Chelsea hot seat lasted just five months, which was purely down to Abramovich’s ruthlessness, but what he accomplished in such a short span of time is nothing short of phenomenal. After excelling with the Blues as a player in the late 90s and early 00s, winning 2 FA Cups, 1 League Cup, 1 Charity Shield, 1 UEFA Cup and 1 UEFA Cup Winners’ Cup, Di Matteo returned to Chelsea as Andre Villas-Boas’ assistant in 2011.

The Italian inherited the Chelsea top job as caretaker after his boss’ sacking eight months later, with the club’s Champions League hopes in serious doubt following a 3-1 loss to Napoli under Villas-Boas. The events that followed are nothing short of Hollywood material. Di Matteo’s galvanised Chelsea proceeded to thrash Napoli 4-1 in the second leg, followed by incredible victories against Benfica and Barcelona in the quarters and semis, setting up a date with Bayern in the final.

Before the final with the German club, Di Matteo lifted his first trophy as Chelsea boss in the form of the FA Cup following an incredible 2-1 victory over Liverpool. If that was a surprise, no one could have predicted what came next. The date was May 19, 2012. The place, Allianz Arena. After two hotly contested halves, the Champions League final was pretty much anyone’s game following goals from Muller and Drogba for either side.

The match dragged on to extra time and could have very much gone Bayern’s way after Chelsea gave away a penalty, but Robben’s shot was saved by Cech. And then the unthinkable happened. Chelsea triumphed over Bayern on penalties, making them the first London club to lift the Champions League and Di Matteo the first Blues boss to win the prize.

The Italian was handed the job on a permanent basis a month later, and after some strong showings in the initial stages of the new season, was sacked when Chelsea’s form trailed off in England and Europe. The decision to sack Di Matteo after just eight months in charge caused widespread controversy amongst the fans, considering the phenomenal job he had done. Nevertheless, his status as a cult hero at Stamford Bridge was sealed, and he will go down as one of Chelsea’s greatest ever managers.

#2 Carlo Ancelotti

The legendary Italian manager was a massive hit at Stamford Bridge, where he proved just why he’s considered one of the all-time greats. Ancelotti, who was announced as the Blues’ new boss on June 1st 2009, won his first trophy barely two months later in the form of the Community Shield by beating reigning league champions Manchester United on penalties.

A string of brilliant performances followed, with Chelsea playing some terrific football under the Italian, who led them to the Premier League title in his debut season – with his team scoring 103 goals, becoming the first Premier League side to score 100+ goals in a single season.

An FA Cup triumph soon followed, with Chelsea securing their first ever domestic double under the Italian. The Blues started the following season strongly, but seemed to falter in the middle while crashing out in the quarter-finals of the Champions League at the hands of Manchester United. Despite leading Chelsea to a second place finish, Ancelotti was relieved of his position on the last day of the season following a 1-0 loss to Everton.

Apart from getting Drogba firing on all cylinders, Ancelotti left Chelsea with the third-highest win percentage in Premier League history – a record surpassed only by Jose Mourinho and Sir Alex Ferguson. All in all, it’s safe to say that the Blues and their flamboyant owner parted ways with the Italian too soon.

#1 Jose Mourinho

Chelsea v Tottenham Hotspur - Capital One Cup Final

Did you REALLY expect anyone else to be on the top of this list?

The charismatic Portuguese proved that he had the cunning to match those immortal words “We have top players and, sorry if I’m arrogant, we have a top manager. Please don’t call me arrogant, but I’m European champion and I think I’m a special one”.

Jose Mourinho was snapped up by Chelsea after leading Porto to an unprecedented double in 2004 – including a Champions League that they won in the most dramatic of circumstances. It didn’t take long for his success to follow him to the shores of England, with Chelsea lifting the domestic double in Mourinho’s first season while setting the record for most Premier League points as well as the fewest goals conceded. The following season started equally well for Mourinho and Chelsea, who went on to lift the Community Shield before winning their second consecutive Premier League title.

The 2006-07 season was disappointing by Mourinho’s standards, but he still managed to lift the FA Cup and League Cup – thus winning every domestic title possible for an English top-flight manager. The Portuguese tactician departed Chelsea unexpectedly in September 2007 following differences with owner Roman Abramovich, but not before sealing his status as the Blues’ greatest ever manager.

Mourinho returned for a second spell at Chelsea in 2013 and lifted the Premier League and League Cup in his second season while overseeing some terrific football before once again departing in 2015 by ‘mutual consent’.

The manager has since been at Manchester United and current club Tottenham with varying degrees of success, but the club Mourinho will always be associated with – not least because of his nickname – is Chelsea. The love affair the Blues have with the Portuguese is just incredible. Somewhere deep, deep down – both of them know that it isn’t quite over yet.

Edited by S Chowdhury