Chelsea Trophies & Titles

There aren’t a huge amount of examples of football clubs whose fortunes have changed entirely because of the arrival of a new owner. When Jack Walker took over at Blackburn Rovers and won them the Premier League is one example. The arrival of Sheikh Mansour and the Abu Dhabi Group at Manchester City is another. Certainly in terms of Blackburn that was a short-lived thing, whilst at the City of Manchester Stadium the takeover may not have been possible if Roman Abramovich hadn’t already done almost the same thing at Chelsea. The Russian’s billions helped the club completely change its story in terms of trophies.

Prior to the arrival of Abramovich, Chelsea had won just one top-flight title, three FA Cups and two League Cups, whilst their experience on the European stage was limited to the UEFA Cup Winners’ Cup and the UEFA Super Cup. Once Abramovich arrived the club added five Premier League titles, five FA Cups, two League Cups and the UEFA Champions League titles, as well as a Europa League and another Super Cup. His work transforming the club’s fortunes also meant that they moved from being also-rans to being in the conversation as one of the biggest clubs in England when the honours were handed out.

League Titles

Prior to Roman Abramovich arriving at Stamford Bridge, Chelsea had won more Second Division titles than they had top-flight ones. That might well help to indicate the state that the club was in before the Russian took over as owner. It wasn’t that they had never won the league, but it is entirely fair to say that their success when it was known as the First Division was entirely different to when it had been rebranded to become the Premier League. In some ways, their success was a sign of exactly what the new-look top-flight was all about, given it was predominantly about the notion of rampant capitalism.

First Division / Premier League

Whereas some clubs have regularly been around the top spot in the top-flight throughout their history, with the likes of Liverpool and Manchester United having won titles or at least challenged for them regularly before they started winning them year after year, Chelsea didn’t even come close until they finished third in 1919-1920.

That was something of a flash in the pan, with their next top three finish actually being when they won it at the end of the 1954-1955 campaign. Another third place finish a decade later than a third in 1969-1970 were the final times that they troubled the top teams until the Premier League era. Here is a look at when they won the league, including information about which teams finished second and how many points separated them:

Season	Points	Second Place	Second Place Points
1954-1955	52	Wolverhampton Wanderers	48
2004-2005	95	Arsenal	83
2005-2006	91	Manchester United	83
2009-2010	86	Manchester United	85
2014-2015	87	Manchester City	79
2016-2017	93	Tottenham Hotspur	86

Second Division

Although the Second Division has also been known as the First Division and is currently called the Championship, it was very much the Second Division during the period of time that Chelsea were successful in it. In fact, they won their two titles in a space of just five years, demonstrating that it wasn’t just the top-flight that they struggled in before having a period of dominance.

Of course, Chelsea supporters are unlikely to be overly disappointed that they don’t have more second tier titles to their name, given the fact that it is not as respected as the First Division or the Premier League. Nevertheless, won it the London club has. Here is a look at their successes in it, alongside the team that came in second and the points achievements of both clubs to give you a sense of whether it was a close-run thing or not:

Season	Points	Second Place	Second Place Points
1983-1984	88	Sheffield Wednesday	88
1988-1989	99	Manchester City	82

The 1983-1984 season was indeed a close one, with Chelsea and Sheffield Wednesday both finishing on 88 points. Chelsea won the title on account of the fact that they had a better goal difference than the Owls, ending up on +50 compared to +38. Five years later and their title win was much more comfortable, though it is interesting to see that the team that they kept at bay to win the Second Division was another club that has benefitted from a rich owner arriving in Manchester City.

Cups & Trophies

For Chelsea, the club was much more likely to win a cup than a title in the pre-Abramovich days. Whether it be on the domestic stage or the European one, the Blues have been able to add trophies to the cabinet on a regular basis throughout the club’s history. They have performed better in some competitions than others, as demonstrated by the number of FA Cups outweighing the League Cups that are in the trophy cabinet. They have also won lesser-known trophies such as the Full Members’ Cup and the UEFA Cup Winners’ Cup alongside the big trophies that garner the attention and respect of the footballing world.

Charity Shield / Community Shield

There will always be a degree of debate regarding whether or not the Community Shield, which was previously known as the Charity Shield before the Football Association were told that they didn’t donate enough money to charity for it to be called that, can be considered to be a big trophy.

We have decided to include it, largely because of the fact that qualification to take part in it has been difficult. Nowadays a club needs to either win the Premier League or the FA Cup to take part in it, or come second in the league if a club does the double. Previously there was different criteria in play, but it was still a tricky thing to be part of. Here is a look at the number of times that Chelsea have won it, alongside the team that the defeated in the match:

Year of Final	Opposition	Scoreline
1955	Newcastle United	3-0
2000	Manchester United	2-0
2005	Arsenal	2-1
2009	Manchester United	2-2*

*For a long time, a Community Shield / Charity Shield game that ended in a draw would simply result in the trophy being shared between the two teams. By 2009, however, a penalty shootout had been introduced to decide the winner, with Chelsea winning that 4-1.

FA Cup

Nowadays, many teams and supporters look down on the FA Cup. It is not considered to be the sort of trophy that teams should put their effort into winning if they are more likely to win the Premier League by correctly using their resources. That hasn’t always been the case, however, and for a long time it was looked on with as much respect as the top-flight title. For a team like Chelsea, who struggled to compete at the top level in England, winning any trophy was seen as a good thing and winning the FA Cup was considered to be a major achievement.

Supporters were delighted to see the club captain loft the trophy above his head any time they won it. Here is a look a the FA Cup wins that Chelsea have enjoyed over the years, alongside information about their opposition and the scoreline:

Year of Final	Opposition	Scoreline
1970	Leeds United	2-1 (a.e.t.)
1997	Middlesbrough	2-0
2000	Aston Villa	1-0
2007	Manchester United	1-0 (a.e.t.)
2009	Everton	2-1
2010	Portsmouth	1-0
2012	Liverpool	2-1
2018	Manchester United	1-0

It is a curious quirk of football that Chelsea’s first eight FA Cup wins didn’t involve a penalty shootout. In fact, the club have lost on penalties more than once, but not won the trophy via penalties. Chelsea’s first FA Cup final appearance came in 1915 when they lost to Sheffield United, with no further appearance until more than 50 years later when they lost 2-1 to Tottenham Hotspur. Their first final appearance of the 1990s was a 4-0 loss to Manchester United, then at the start of the 2000s they lost 1-0 to London rivals Arsenal.

They lost again to to the same opposition 15 years later, then again in 2020 before a 1-0 loss to Leicester City and a loss to Liverpool on penalties completed an unwanted hat-trick of FA Cup final losses in consecutive years.

League Cup

The League Cup is another competition that has gone through numerous different forms of respect from the big teams. It is the first trophy that a side can get into the cabinet, with some managers seeing it as a good opportunity to add silverware before the season has even really got going.

That is very much how José Mourinho seemed to treat the competition when he was in the Chelsea dugout, regularly winning it in order to confirm some silverware for his team. Winning begets winning, which is why the fact that the League Cup isn’t held in much regard to some people is seen as irreverent to those that win it. Here is a look at Chelsea’s wins, along with information about their opposition and the scoreline:

Year of Final	Opposition	Scoreline
1965	Leicester City	3-2 aggregate
1998	Middlesbrough	2-0 (a.e.t.)
2005	Liverpool	2-3 (a.e.t.)
2007	Arsenal	2-1
2015	Tottenham Hotspur	2-0

Chelsea’s first League Cup final appearance came at a time when it was played over two legs, defeating Leicester City 3-2 in the first-leg and then drawing 0-0 in the second. Seven years later they played Stoke City and lost 2-1 when it was just a one-off match. They then weren’t on the losing side again until a 2-1 loss to Tottenham Hotspur in 2008 when they were the defending champions. They lost in the final three times in five years, being defeated on penalties by Manchester City in 2019, on penalties by Liverpool in 2022 and by Liverpool again in extra-time in 2024.

Champions League

For the majority of the competition’s existence, the Champions League was known as the European Cup. In the case of Chelsea, the club didn’t really start appearing in it until after the rebrand, with all of their wins coming in the Champions League era. They also came extremely close to appearing in more finals than they have, being losing semi-finalists against Liverpool in both 2004-2005 and 2006-2007.

They also lost in the final against Manchester United in the 2007-2008 season. It is a competition that Chelsea have struggled in more than some other English clubs, but still have the trophy in the cabinet. Here is a look at their wins, including the opposition and the scoreline:

Year of Final	Opposition	Scoreline
2012	Bayern Munich	1-1*
2021	Manchester City	1-0

*The match ended 1-1 in 90 minutes and no further goals were scored in extra-time, meaning that it went to penalties. Chelsea won 4-3, with Juan Mata missing their opening penalty before both Ivica Olić and Bastian Schweinsteiger failed to score for the Germans.

Europa League

Nowadays, the Europa League is seen as the less important brother of the Champions League. It is often looked down upon by clubs that are able to compete in the European Cup, but the truth is that it used to garner a lot more respect when it was known as the UEFA Cup. All of Chelsea’s wins in it have come in the Europa League era, but their success was no less enjoyable for the supporters because of that.

In actual fact, the only thing that dampened the enjoyment of supporters when they won it for the first time was the fact that the manager was Rafael Benítez, who had been a thorn in their side as Liverpool manager. Here is a look at their Europa League wins, including the opposition and the scoreline:

Year of Final	Opposition	Scoreline
2013	Benfica	2-1
2019	Arsenal	4-1

Other Noteworthy Trophies

There are many that would point to some of the other trophies that Chelsea have won over the years and say that they are just as worthy of discussion as the big ones we’ve talked about already. The Full Members’ Cup, for example, was brought into being in the wake of English clubs being banned from European competition after the Heysel Stadium Disaster, so some feel that it carries the same weight as a European trophy.

The UEFA Super Cup and FIFA Club World Cup, meanwhile, can only be won if you have also won the Champions League or Europa League, making them more valid versions of the Community Shield. Here is a look at how Chelsea have done in various competitions over the years, including the opposition and the scoreline:

Competition	Year of Final	Opposition	Scoreline
Full Members’ Cup	1986	Manchester City	5-4
Full Members’ Cup	1990	Middlesbrough	1-0
UEFA Cup Winners’ Cup	1971	Real Madrid	2-1*
UEFA Cup Winners’ Cup	1998	VfB Stuttgart	1-0
UEFA Super Cup	1998	Real Madrid	1-0
UEFA Super Cup	2021	Villarreal	1-1**
FIFA Club World Cup	2021	Palmeiras	2-1 (a.e.t.)

*The UEFA Cup Winners’ Cup final of 1971 originally ended in a 1-1 draw, which meant that a replay was needed to decided upon the winner. It was played two days later in front of just shy of 20,000 people, compared to the 45,000 people who had attended the original final.

**The UEFA Super Cup final in 2021 ended in a 1-1 draw after 90 minutes, with no further goals scored in extra-time. As a result, the game went to penalties and Kai Havertz missed the opening one for the Blues. Thankfully for the London club, Aïssa Mandi and Raúl Albiol both missed their penalties for the Spanish side, handing Chelsea the win.