Claudio Ranieri
Tenure: 2000 to 2004
Record: 95-44-45
The first manager under Abramovich, Claudio Ranieri had just one season at the club under the new ownership. Ranieri had done well with the Blues in the years leading up to the club’s sale. He led them to the 2002 FA Cup final and slowly moved them up the league, in addition to guiding the breakthrough of one John Terry and purchase of Frank Lampard. Under Abramovich’s watchful eye, Ranieri’s Chelsea finished second in the Premier League behind only Arsenal’s Invincibles—a noble feat given how the Gunners were on an entirely different level that season.
Ranieri also led Chelsea to the Champions League semifinals, beating Arsenal in the quarterfinals, but his decision making against Monaco cost him his place at the club. With Chelsea drawing 1-1 in the first leg and with a man advantage, Ranieri would make negative substitutions allowing Monaco back into the game to score two more before the match was up. In the second leg, a 2-0 lead—which would have seen Chelsea reach the final—was ultimately surrendered and saw Ranieri tarnished. He won zero trophies during his time at the club, but the Italian laid the foundation for greater things to come.
Guus Hiddink
Tenure: 2009; 2015 to 2016
Record: 26-16-7
The first Chelsea interim manager under Abramovich, Guus Hiddink had two spells at the club, but the most noteworthy one was his first. Losing just one game from 22 under Hiddink (a 1-0 defeat to Tottenham) the Blues pushed hard for another Premier League title under the Dutchman, but they were ultimately too far off when he was appointed.
However, Chelsea did find glory in the FA Cup, beating Everton 2-1 at Wembley. The Blues were close to reaching a second-consecutive Champions League final, as well, but a 1-1 draw with Barcelona dashed their hopes. Hiddink’s spell at the club led fans to hope and chant for his permanent stay, but the manager left at the end of the season to continue his role as manager of the Russian National Team, which included a run to the semifinals of Euro 2008.
Maurizio Sarri
Tenure: 2018 to 2019
Record: 38-14-11
Maurizio Sarri enjoyed a good start to life in London, going unbeaten in his first 12 Premier League games. Chelsea was playing exciting, attacking football, but that form soon tailed off rather spectacularly. Questions about how long Sarri would last at Stamford Bridge were answered shortly after as the 60-year-old left the Blues after a spell of just one full season. Sarri did manage to depart with his first ever major trophy as a manager—the Europa League—with a convincing 4-1 win over Arsenal.
Roberto Di Matteo
Tenure: 2012
Record: 25-8-9
A man who was originally brought in just to see out the season following Andre Villas-Boas’ departure, the former Villas-Boas assistant went on to lead the club to its first ever Champions League trophy—a really astonishing feat. Turning back to the veterans that Villas-Boas had tried to push out, one of Di Matteo’s first tasks was to record a rarely seen two-goal comeback in the Champions League to Napoli, before Benfica and Barcelona fell. Then came Bayern Munich in the final at the Allianz Arena, just two weeks after Chelsea had lifted the FA Cup with a penalty shootout win giving the club their only European Cup.
The Blues finished sixth in the Premier League, however, and only qualified to the following season’s Champions League as a result of winning the competition. Nevertheless, their defence lasted just up until the group stages as they were demoted to the Europa League and Di Matteo sacked following a poor start as permanent manager.