Ten Years Of Chelsea Managers: Grading The Best And The Worst

A look back at the managers of Roman Abramovich’s ten-year reign at Stamford Bridge.

Claudio Ranieri

When Roman Abramovich arrived at Stamford Bridge, Claudio Ranieri had been there for three years, and looked to be doing a reasonable job with the club. However, expectations were very different with the injection of the wealthy Russian’s money, and it was unclear if Ranieri would survive long under the club’s new ownership.

The Italian got busy pretty quickly, spending Abramovich’s millions on the likes of Hernan Crespo, Claude Makelele, Damien Duff, Joe Cole, Juan Sebastian Veron and Adrian Mutu. These success of these signings was rather mixed, though they did help Chelsea climb the table from a finish of 4th in 2002/03 to 2nd in 2003/04, behind only Arsenal’s famous ‘Invincible’ side. The Blues also managed to progress to the Champions League semi-finals, though they were disappointing in their exit to unfancied French side Monaco. Ironically, the final that year between Didier Deschamps’ side and Jose Mourinho’s Porto was seen as a battle for the Chelsea job, as Ranieri looked likely to be punished for failing to deliver instant silverware to Abramovich. Porto won the final and Mourinho was indeed selected as Ranieri’s successor, despite Chelsea’s marked improvement in achieving their record points total and best defensive record in the Premier League.

Final grade: C-

Although he perhaps wasn’t given enough time to take Chelsea further, almost the same group of players went on to achieve much more success just after his departure, suggesting perhaps that he wasn’t able to get the best out of them. His deserved reputation of tinkering too much with his squad also worked against him, as he needlessly changed his team around too often, not allowing them to develop better chemistry as a team.

Jose Mourinho

Mourinho was much admired for his work with Porto, exceeding all expectations in winning the Champions League with the Portuguese side, and looked an excellent appointment to take Chelsea to the next level. He announced himself as a ‘special’ manager on his arrival, and so that proved to be. In his first season – no doubt aided of course by the funds to bring the likes of Didier Drogba, Petr Cech and Arjen Robben – he delivered instant success with the Premier League title, achieved with a record points total of 95 and a best-ever defensive record of just 15 goals conceded. Along with that, there was a win in the Carling Cup final against Liverpool.

In his next season, he brought the highly influential Michael Essien to the club, and maintained Chelsea’s dominance as they retained the league title, which was sealed with an impressive 3-0 win over Manchester United at Stamford Bridge. Under his guidance, the likes of John Terry, Frank Lampard, Joe Cole and Didier Drogba were starting to grow into some of the best players in the world.

However, Mourinho was unable to win a third title in a row, as some poor signings in the form of Andriy Shevchenko, Michael Ballack and Salomon Kalou were made (though it is generally thought that Shevchenko was signed against his will by Abramovich), allowing Manchester United to improve and win the league in 2006/07. The Blues didn’t finish empty-handed though, as they gained revenge on Sir Alex Ferguson’s side with a 1-0 win over them in the FA Cup final.

Despite being by far the club’s most successful manager, Mourinho was seemingly forced out by Abramovich early in the 2007/08 season after a poor start and rumours of friction in their relationship.

Final grade: A

The only thing missing was Champions League success which Abramovich so greatly craved, but there’s no doubt Mourinho’s influence at Chelsea lasted long after he left, instilling a new-found winning mentality which had often eluded them under Ranieri. His teams were not known for playing entertaining football, but no one else got results quite like he did.

Avram Grant

Grant took charge of Chelsea for most of the 2007/08 season following the surprise departure of Mourinho. The Israeli was not a popular appointment with the club’s fans due to his lack of top-level experience, and it later emerged that many of the Chelsea players didn’t respond well to his methods either.

However, despite his short time in charge of the club, he managed to have a fairly memorable impact. He took them to the final of the Carling Cup, though he was under pressure after his side lost 2-1 in extra time to underdogs Tottenham. Manchester United again won the Premier League, though Chelsea’s fine end-of-season form pushed them all the way for the title, and they even managed to reach the Champions League final, coming up against their title rivals once again in the first-ever all-English European Cup final tie. Grant’s side gave a good account of themselves, and were arguably the better team in Moscow, but were beaten by United in a penalty shoot-out, with John Terry famously slipping and mis-hitting the crucial penalty that would’ve won them the game.

Many feel Grant wouldn’t have even kept his job if Chelsea had won the Champions League, as he continued to provoke skepticism over his abilities to get the best out of this Chelsea side. As it was, he was sacked three days after the final.

Final grade: C-

Although he did well to take Chelsea to their first Champions League final, the Carling Cup final defeat was unacceptable, and there was certainly the feeling that he failed to get enough out of a clearly talented Chelsea team. His later stints with Portsmouth and West Ham also suggest he is not really a top level manager, as he got the two sides relegated from the Premier League.

Luiz Felipe Scolari

Replacing Avram Grant was Luiz Felipe Scolari, who had become famous in recent years for knocking the England national team out of major tournaments. Scolari was a World Cup winner with Brazil, and had also done good work with Portugal. After knocking England out of three consecutive international tournaments, the FA had approached him to take over as their manager, though he is understood to have rejected them.

This attention in England with hindsight perhaps over-estimated his actual abilities as a manager, as his short-lived spell with Chelsea was not a successful one. He lasted only until February, with his team looking poor defensively and well out of the title race. Many cited his lack of experience at club level, and many Chelsea players seemed to go backwards under his training methods. His main signings of Deco and Jose Boswingwa also proved to be relatively poor ones, as neither properly settled in English football.

Final grade: D

This very short spell in charge is one of the more understandable ones of the Abramovich era. Although it is good to give managers time, Scolari was clearly the wrong choice for Chelsea and it was a wise decision to part with him when they did, as things quickly picked up under his successor.

Guus Hiddink

Left to pick up where Scolari left off was Dutch coach Guus Hiddink, who had earned a great reputation for his work with the national sides of South Korea, Australia and Russia, taking unfancied nations much further than they seemed capable of. Abramovich was keen to take him on permanently, though he remained committed to his work with the Russian national team, and made it clear he would only take charge of Chelsea until the end of the 2008/09 season.

In his short time, he made a great impact. The team looked much better than they had done under Scolari, and managed to finish in a credible 3rd place in the Premier League, as well as winning silverware with an FA Cup final victory over Everton. They were also denied of a second successive appearance in the Champions League final on away goals after a controversial game against Barcelona, in which the visitors seemed to get all the luck with refereeing decisions.

It would have been interesting to see how much further he could have gone with the Blues, but he remains popular with the club to this day for his time at Stamford Bridge.

Final grade: B

Did as much as he could do in such a short space of time. Hiddink got the team back to their best after a difficult first half of the season, got them playing good football, and brought home some silverware after they’d fired a blank the year before.

Carlo Ancelotti

Carlo Ancelotti became Chelsea’s fifth manager in three years after taking over from Guus Hiddink at the start of the 2009/10 season. He had been linked with the club before following his fine work with AC Milan, and it turned out to be a good move by Abramovich after failing to secure the permanent services of Hiddink.

Ancelotti introduced a more attacking approach to the Chelsea team, and that season they played some of the best football in the country. They weren’t always as solid as they had been under Jose Mourinho, but they achieved great success as a record-breaking 103 league goals saw them win the Premier League title again for the first time for four years, as well as beat Portsmouth 1-0 in the FA Cup final to complete the first ‘double’ in their history. All this was achieved without any significant spending of Abramovich’s money, choosing continuity over the club’s previous methods of simply trying to bring in as many star players as possible. They were disappointing in the Champions League though, as they were eliminated by Mourinho’s Inter Milan side, who later went on to win the tournament.

Ancelotti’s second season was not so successful. Having started well, Chelsea slipped up in the middle of the year due to Abramovich’s meddling with first-team affairs. Ancelotti’s assistant manager Ray Wilkins was sacked against his will, and Fernando Torres was signed for £50million in the January transfer window despite being seen by many as being past his best. Torres failed to settle, scoring just one goal that season, and Ancelotti was unsurprisingly sacked as the team failed to win a trophy. For no obvious reason, it became clear that Abramovich was not happy with him, and wanted a change.

Final grade: B+

Ancelotti was very unfairly treated by Chelsea and probably looked like their best managerial appointment since Mourinho. If left to take full control of the team he could well have secured the title again, as it was only after Abramovich’s interfering that results started to go down hill. No other manager got Chelsea playing such good football, and he has gone on to enjoy success at PSG and probably soon Real Madrid.

Andre Villas-Boas

Dubbed ‘the next Mourinho’ after his great success with Porto, Chelsea made Andre Villas-Boas the most expensive manager of all time after bringing him to Stamford Bridge to replace Carlo Ancelotti. Despite much anticipation after his arrival, the Portuguese coach was another to not last long under Abramovich at all, though he was there for marginally longer than Scolari, eventually being sacked in March 2012 after a 1-0 defeat to West Brom.

Results were mixed under AVB, and he perhaps tried to change too much too fast at Chelsea, leaving key, experienced members of the team out for no obvious reason and making drastic changes to the playing style at the club. Once the most solid team in the country under Mourinho, Chelsea had some bizarre results such as a 5-3 home defeat to Arsenal and 3-3 draw with Manchester United from 3-0 up. Although a talented manager, he and Chelsea simply weren’t a good fit and it is understandable why he was sacked when he was. He has since gone on to take charge at Tottenham, and is arguably yet to win some of the fans over at White Hart Lane as well.

Final grade: D

Along with Scolari, a poor time in charge of Chelsea. AVB was overly ambitious to change the entire mentality of the team, ignoring its obvious strengths and trying too hard to do everything his own way. His methods were unpopular with many of the senior players, and unfortunately for him, the results on the pitch backed them up.

Roberto Di Matteo

Andre Villas-Boas was replaced by his assistant Roberto Di Matteo, who was a fans’ favourite at Stamford Bridge from his time as a player. The Italian was not the big name appointment everyone was expecting though, and was relatively inexperienced as a Premier League manager, with only a disappointing spell at West Brom to speak of.

However, this young manager was quickly one of the most talked about names in Europe, after picking up a poor-looking Chelsea team and guiding them to the Champions League final. After some incredible defensive performances and displays of team spirit, they overcame tournament favourites Barcelona in the semi-finals, and then worked their magic again to grind out victory against Bayern Munich in a penalty shoot-out. Some were critical of Chelsea’s tactics in that run, but there can be no doubt Di Matteo had worked wonders with a team that was going nowhere under AVB.

Going into the next season, Di Matteo started to exert his influence on the Chelsea team more, bringing in skillful attacking players like Eden Hazard and Oscar, which made Chelsea early favourites for the title after a superb start to the season. Defensively organised and technically gifted, the Blues looked almost perfect under his guidance, and he was very harshly sacked after a quick run of disappointing results. One feels he would have been given more time had he been a bigger name, but Abramovich seemed hesitant about hiring him even after the Champions League win.

Final grade: B+

Another very harsh sacking. In a short space of time Di Matteo transformed a struggling side into champions of Europe against all the odds. He also showed he was tactically flexible with his switch from a defensive game in 2011/12 to a more attacking game in 2012/13, and he pulled both of these off perfectly. There weren’t many bad results, but they were apparently enough to cost him his job.

Rafael Benitez

In what was a very unpopular move by Abramovich, the Russian owner appointed former Liverpool boss Rafael Benitez as the club’s next manager. The Spaniard started poorly, and was probably not helped by the continuing poor reception he received from supporters at Stamford Bridge. It was hard for many to see why Benitez was seen as a better option than Di Matteo, though Abramovich at least made it clear he was only being brought in on a temporay basis before choosing the club’s next appointment.

Despite inheriting a difficult situation, Benitez did manage to win silverware, guiding Chelsea to a win in the Europa League final against Benfica, winning over some of the fans along the way. He failed to get their title challenge back on track though, as they only managed to finish third in the Premier League.

Final grade: C

Benitez always divides opinion, and it’s hard to know if he could have done more with this Chelsea team. He certainly didn’t look like an upgrade on Di Matteo, but he did his job in terms of winning a trophy and securing Champions League football for next season.