Highlights

• Chelsea have struggled immensely since the end of the Roman Abramovich era, falling out of the country's top 10 sides.
• Three out of the 10 defeats on this list have occurred after 2020, while nine have happened since 2000.
• A six-goal defeat to Manchester City and five-goal loss to Arsenal are among the most embarrassing for Chelsea in the Premier League era.

Even a football club the size and stature of Chelsea has their bad days. Forget the stacked trophy cabinet and the memorable wins they’ve enjoyed over the years; it is often the sporadic thumpings that are best remembered.

Roman Abramovich’s arrival in 2003, coupled with his injection of cash, meant that these became far less commonplace, but their Premier League era has, of course, been littered with the odd calamity – just like every other side in the top flight.

This got us thinking here at GIVEMESPORT about some of the worst defeats that the Blues have been on the receiving end of over the years. For all of their triumphs and trophies, they haven’t been immune to being humbled every once in a while. So here are the 10 most embarrassing defeats Chelsea have suffered in Premier League history.

10 Chelsea 1-3 Liverpool

October 31st 2015

It’s rather fitting that such a horrifying game for both Chelsea and then chief Jose Mourinho, one of the best managers in England top flight history, took place on Halloween. Fundamentally, when you end up losing your job because of a result, you know that it simply needs to end up on a list of the club's most embarrassing losses.

For context, Chelsea had taken 11 points from their first 30, while Liverpool weren’t much better with 14 points and their new manager, Jurgen Klopp, hadn’t won a league match since taking over the club. However, by the end of the game, it was clear that a new, exciting era was arriving at Liverpool, while it was the end of one at Chelsea and one that, judging by the form at the time, should have ended a long time before.

9 Chelsea 1-4 Brentford

April 2nd 2022

The 2021/2022 season was a big one for Brentford as it was their first-ever venture into the top flight of English football since the 1940s, so it’s no surprise that teams were licking their lips when they got the chance to play them. However, Chelsea didn’t know what hit them when they played them at Stamford Bridge.

The days of Stamford Bridge being a fortress seemed like a distant memory when the newly promoted Brentford put four past the European and World Champions in April 2022, firmly cementing themselves as a Premier League team, and putting a dark cloud over Chelsea’s home for a day at least.

8 Chelsea 2-4 Manchester City

February 27th 2010

Well, this one was an eventful one. Chelsea finished the 2009/2010 season as Premier League Champions and FA Cup winners, with many considering this to be arguably the team’s best season as a whole. But that doesn’t mean it didn’t have its speed bumps along the way.

Beginning with Wayne Bridge embarrassing John Terry by ignoring his handshake, the game eventually descended into a disaster for Chelsea as City put four goals past Hilario, both Michael Ballack and Juliano Belletti got themselves sent off, and proved that while they might be able to cross the line, they were still vulnerable along the way.

7 Liverpool 5-1 Chelsea

September 21st 1996

Anfield has always been a difficult place to play, even in Liverpool’s most difficult periods, but this was during a time in Chelsea’s history when they were making their case as the next big team to worry about in the Premier League. So getting beaten so badly by one of your new rivals isn’t going to be a good look.

Ruud Gullit’s men were given something of a reality check by Roy Evans’ Liverpool side as they conceded five goals away from home. They did get a consolation at the end of the game which covered up part of the poor performance, but had they not won the FA Cup a few months later, this might have been one of the more memorable parts of Chelsea’s 1996/1997 season.

GIVEMESPORT Key Statistic: Chelsea's worst-ever defeat (8-1) came against Wolverhampton Wanderers on 26/09/1953.

6 Watford 4-1 Chelsea

February 5th 2018

Chelsea’s defence of the Premier League title in 2017/2018 started off on the wrong foot, losing at home to Burnley, which set the tone for the whole year. People kept asking if they would qualify for the Champions League, would the new signings ever find their form, and how long it would take before the revolving door of managers at Stamford Bridge began spinning again, and this trip to Watford certainly didn’t help matters.

Another game that was hampered by the fact that Chelsea went down to 10 men after 30 minutes, and to their credit they fought back well with the game being level at 1-1 with seven minutes to play. However, a complete collapse that saw them concede three goals in eight minutes against a team who were still technically in a relegation fight is never good for the image of a team like Chelsea.

5 Bournemouth 4-0 Chelsea

January 30th 2019

It’s hard to pinpoint what happened in 2019, but Bournemouth somehow became Chelsea’s bogey team. The Cherries had only won three out of the 14 previous games against Chelsea in a head-to-head record that dates back to 1989, so to celebrate the 30th anniversary of their first meeting, Bournemouth decided to win by the biggest margin in the fixture’s history.

Eddie Howe’s side held firm in the first half before completely demolishing The Blues in the second half, putting four past them and putting a limited amount of time on Maurizio Sarri’s time as Chelsea manager in the process. It was certainly one of the darker days they had under the Italian's stewardship, as fans began to turn on him following the match.

4 Leeds United 3-0 Chelsea

August 21st 2022

While the rivalry is not as ferocious as it once was, losing still stings. Revered as what kicked off their recent downfall, Chelsea's trip to Elland Road at the start of the 2022/23 campaign ended 3-0 in favour of the Whites, and the fans and players alike travelled back down to London in utter disbelief.

This defeat to Leeds United was Chelsea's first of 16 for the 2022/2023 season. Kalidou Koulibaly was sent off, fans continued to get on Thomas Tuchel’s back, and the German coach was eventually sacked a few weeks later. Even though the 4–1 losses to both Brighton and Manchester United might seem worse on paper, you could argue that those results stemmed from this trip to Yorkshire.

3 Manchester United 4-0 Chelsea

August 11th 2019

It was the dawn of a new era. One of the club's most beloved players has returned to manage the team he became synonymous with. The first game of the new season was against one of the club's biggest rivals of the 21st century. If everything goes well, it could go down as one of the most memorable matches in club history. What could go wrong?

Rather than having a fairytale start to his time as Chelsea manager, Frank Lampard was embarrassed by Manchester United, who also needed a good start to the season after their disastrous end to the previous one. Two goals from Marcus Rashford, plus goals for Anthony Martial and Daniel James kicked the Chelsea icon's time off as manager in the worst possible way, and judging by the fact that the club seemed to do a lot better after his departure in 2021, it was a sign of things to come.

2 Arsenal 5-0 Chelsea

April 23rd 2024

It’s never fun losing to your rivals, but losing 5-0 just adds salt to the wounds. Unfortunately for those of a Stamford Bridge persuasion, that’s exactly what happened when Mauricio Pochettino’s European-chasing side faced one of the favourites for the title, Arsenal.

From start to finish, the Blues looked second best and former Blues ace Kai Havertz managed to bag a brace. At the time of writing, the two clubs are at entirely different ends of the spectrum in terms of their journeys and the chasm in talent is evident. Questions have been asked of the Argentine tactician after the defeat and, on the basis that they do not finish the campaign on a high, his role could be at risk.

1 Manchester City 6-0 Chelsea

February 10th 2019

An easy number one as it is one of Chelsea’s biggest losses in the club’s history, let alone in the Premier League. It’s fairly common nowadays to see Manchester City putting six goals past an opponent regardless of the competition, but when it happens to a team that are supposed to be one of your biggest competitors, it will always get remembered by both teams.

By this point in the 2018/2019 season, Chelsea had fallen away from the title picture, as Manchester City and Liverpool decided to become the two best teams in the world and create their own little mini-league at the top of the table. In the midst of all this, Chelsea had to travel to the Etihad and were thumped 6-0 with four of those goals coming in the first half and three of them going to Sergio Aguero, one of the Premier League's top goalscorers of all time. Had they not won the Europa League a few months later, this would have been the most memorable part of a disappointing season for Chelsea.