Chelsea has won a healthy number of prestigious awards in its time. Its first major honour was the League Championship – now known as the Premier League – in 1955. The club’s first FA Cup came in 1970 while their first European triumph was the UEFA Cup Winners’ Cup in 1971.
Domestically, the Blues have won six Premier League titles, eight FA Cups, five League Cups, and four FA Community Shields. Internationally, they have won the UEFA Champions League twice, the UEFA Europa League twice, the UEFA Cup Winners’ Cup twice, the UEFA Super Cup twice, and have once won the FIFA Club World Cup.
In terms of overall trophies won Chelsea is the joint fourth-most successful club in English football. Most of these achievements have been collected within the past two decades. And within that time frame, Chelsea has appointed 21 managers – including interim and caretaker managers – a fact that has now become more of a talking point than their achievements.
José Mourinho: June 2004 to September 2007
José Mourinho earned his iconic nickname, ‘The Special One’ during his first tenure at Chelsea, and rightfully so. Mourinho brought glory back to Chelsea, as he and the Blues created an unforgettable legacy together.
June 2003, was the start of a new era for Chelsea – the Abramovich era. Claudio Ranieri was the first manager to work under Roman Abramovich, with Raineri being manager since 2000. At the end of the 2004 season, the club let Ranieri go despite Chelsea finishing runners-up behind Arsenal’s ‘invincibles’ and reaching the UEFA Champions League semi-final.
The man who was called up to replace Ranieri was Mourinho.
Mourinho proved his worth instantly. With his introduction of the 4-3-3 formation from the 4-4-2 diamond paired with a team stacked with top players and a top manager, Chelsea went on to have an unforgettable 2004/05 season. Chelsea won the Premier League title for the first time in 50 years that season with a record-breaking 95 points. They conceded only 15 goals throughout the entire campaign – a record yet to be broken.
That same season, Mourinho lifted more silverware. In addition to the Premier League title, the EFL Cup and FA Community Shield were his two by the end of his first season at Chelsea.
The following season, after 29 wins like their the previous season, Mourinho won the Premier League title yet again. A win against their closest rivals Manchester United 3–0 at Stamford Bridge towards the end of April confirmed the Blues as champions.
Mourinho’s third season at Chelsea was set to be the most magical of them all. Chelsea was in the race to win a quadruple up until the closing weeks of the season. The 2006/07 Premier League title winner was decided after Chelsea failed to win against Arsenal. A draw left them seven points behind Manchester United with two games to go. There and then Manchester United was confirmed to be the league champions.
Chelsea lost in the UEFA Champions League semifinals to Liverpool in a penalty shootout. So after a long season of decent performances and high expectations, all that Chelsea walked out with that season was the FA and EFL Cups.
Seven games into the 2007/08 season, Mourinho was dropped by Chelsea. In those seven games, Chelsea had a 3-2-2 record. His last game during this tenure was a draw against Rosenborg in the group stage of the UCL.
Avram Grant: September 2007 to May 2008
Avram Grant was called up to replace Mourinho from 20 September onward. Grant’s first match was against defending champions, Manchester United. He lost the game 2-0.
However, the momentum picked up following that loss. In his next 43 games, he led Chelsea to 28 wins, 12 draws and 3 losses in all competitions. The most significant loss came from Chelsea’s first appearance in the Champions League final. The game against Manchester United ended in a draw, leaving it to a penalty shootout, which the Red Devils took.
Chelsea went the entire 2007/08 season without a single loss at home. Despite this, it was the first season in four years that Chelsea had finished the season without a trophy. Nonetheless, it was a good season for the Blues. However, Abramovich’s standards were high, and the lack of silverware led to Avram Grant being sacked three days after the Champions League final.
Felipe Scolari: June 2008 to February 2009
Avram Grant’s replacement was Luiz Felipe Scolari. The Brazilian had just managed the Portugal national team at UEFA Euro 2008, getting them to the quarterfinals.
The Brazilian introduced a narrow 4–1–4–1 formation that had Chelsea top of the league table after his first 13 Premier League games in charge. In those 13 games, the Blues had won 10, drawn twice and lost only once.
His next 12 Premier League games were a complete contrast to the previous ones. Chelsea went 4-5-3 in that run. Among these losses was Chelsea’s first Premier League loss at home league game since 2004 – 86 matches – when they lost to Liverpool. Another one of those losses was a second home league defeat to Arsenal. In that same run, Chelsea had been kicked out of the fourth round of the EFL Cup by Burnley on penalties at Stamford Bridge.
Felipe Scolari was the second Chelsea manager to be sacked that season.
Ray Wilkins: February 2009
Assistant Manager Ray Wilkins was appointed as Caretaker Manager before Chelsea found a suitable replacement for Scolari.
He was only in charge for one game, which turned out to be a fifth-round FA Cup 3-1 win against Watford.
Guus Hiddink: February 2009 to May 2009
Guus Hiddink was appointed to head the Blues for the remainder of the 2008/09 season as Interim. Within his 13 Premier League games, he won 11, of the 13 matches, drawing once and losing the other. It was a composed takeover by the Dutchman, with a 4–1 victory over Arsenal away at the Emirates making a statement.
His short but successful run secured third place in the league for the Blues, and Champions League football for a seventh consecutive season. He reached the Champions League semifinals, where Chelsea was drawn against Barcelona. Chelsea put on a good performance, but it was overshadowed by controversial referring which saw Chelsea get knocked out.
Hiddink managed to secure silverware for the Blues when they beat Everton in the FA Cup finals, concluding his time at Chelsea with a huge positive.