To be a Chelsea fan means to be ready for moments of very “high” highs and depressing lows.
Chelsea are known as the “Pride of London”. They are seen as the biggest club in London, but that doesn’t exempt them from the excruciating heartbreaks that comes with football. In this article, we look at the top five moments in Chelsea’s history that have a core, sad moment among the fanbase.
1. The Slip in Moscow (2008 Champions League Final)
There is no image more synonymous with Chelsea heartbreak than a rain-soaked John Terry sitting on the turf of the Luzhniki Stadium, head in hands.
After years of falling at the semi-final hurdle, Chelsea finally reached the summit in 2008 against domestic rivals Manchester United.
📅 On this day, in 2008, Manchester United beat Chelsea on penalties in a dramatic Champions League final in Moscow..
I don’t think Manchester United fans will ever get bored of watching that John Terry slip! 😅 pic.twitter.com/zZAgWWx1Fu
— Football Tweet ⚽ (@Footballtweet) May 21, 2025
The match was a grueling 1-1 affair that bled into a penalty shootout. When Cristiano Ronaldo missed his spot-kick, the stage was set: Terry, “Mr. Chelsea” himself, only had to convert the fifth penalty to crown his club Kings of Europe. As he stepped up, the Moscow heavens opened. Terry slipped at the point of contact, his standing leg giving way as the ball clipped the post and sailed wide. The dream vanished in a literal heartbeat, and United eventually triumphed in sudden death.
A moment Terry and many Chelsea fans who witnessed that game won’t forget forever, even though they had Champions League triumphs in 2012 and 2021.
2. “A Disgrace”: The Ovrebo Scandal (2009 Champions League Semi-Final)
If 2008 was about bad luck, 2009 was about a perceived injustice.
Facing Pep Guardiola’s legendary Barcelona at Stamford Bridge, Chelsea put in a tactical masterclass. Leading 1-0 through a Michael Essien thunderbolt, the Blues were denied what appeared to be four stone-cold penalties by referee Tom Henning Ovrebo.
That 2009 UCL night at Stamford Bridge still feels unreal 😤
Chelsea were denied not one, not two, but several clear penalties against Barcelona — and after Iniesta’s late screamer, Drogba lost it on live TV shouting “It’s a disgrace!” 😭Was that the biggest robbery in football… pic.twitter.com/iQV48zaoHL
— Prince 👑 (@Princeutd1P) November 14, 2025
From Gerard Piqué’s blatant handball to Samuel Eto’o blocking a goal-bound shot with his arm in stoppage time, the whistles never came. In the 93rd minute, Andres Iniesta struck a dagger into the top corner with Barcelona’s only shot on target. The sight of Didier Drogba screaming “It’s a disgrace!” into the television cameras became the iconic image of a night where Chelsea felt the sport itself had conspired against them.
Anytime the conversation of poor officiating comes up, Chelsea fans will always remember that night. It was actually “a disgrace.”
3. The Relegation Battle of 1988
Long before the glitz of the Premier League, Chelsea faced a darker reality.
In the 1987-88 season, the club finished 18th in the First Division and were forced into a promotion/relegation play-off against Middlesbrough. After losing the first leg 2-0, a desperate Chelsea won the return leg 1-0 at Stamford Bridge but lost on aggregate.
The final whistle triggered scenes of absolute despair and chaos. Fans invaded the pitch, and the realization that a club of Chelsea’s stature was dropping to the Second Division was a bitter pill for a generation of supporters. Although this wasn’t the first time Chelsea had been relegated, in fact, they had been relegated five times before 1988, but in 1988, they were seen as part of the top clubs in England, and the relegation was a cloak of shame.
It was a moment of existential crisis that served as the “rock bottom” from which the modern club eventually rose.
4. The 2020-22 FA Cup Final “Triple Heartbreak”
Chelsea’s recent history in the FA Cup has been a lesson in psychological endurance. Between 2020 and 2022, the Blues lost three consecutive FA Cup finals. However, the 2022 defeat to Liverpool was particularly agonizing.
Chelsea the first team to lose back to back FA Cup Finals since Newcastle (‘98, ‘99) #FACupFinal pic.twitter.com/ay2lIAql1i
— talkSPORT (@talkSPORT) May 15, 2021
After 120 minutes of high-octane football that ended 0-0, the match went to penalties, just as the Carabao Cup final had months earlier against the same opponent. When Mason Mount’s penalty was saved and Kostas Tsimikas converted for Liverpool, Chelsea became the first team in history to lose three consecutive FA Cup finals. To play so well and come away with nothing three years running felt like a curse.
It became more annoying as the term “billion dollar bottlejobs” was peddled by Gary Neville. Chelsea fans were dealing with the fact that their darling Abramovich was forced out of the club due to his involvement with the Russian government.
Gary Neville: “I wish I had not said billion dollar bottle jobs, They’re harsh lines that stain a group of players or a manager” (Stick to Football Podcast) #CFC pic.twitter.com/egBM1Jeoju
— Pys (@CFCPys) December 19, 2024
Chelsea weren’t happy with their new owners, who were more keen on spending heavily than actually building the club. They won the UEFA Champions League in 2021, but Thomas Tuchel, who had endeared himself to the fans with the way he handled the club during the takeover, was later sacked. For many Chelsea fans, a part of their love for the club died that day, even more painful than the FA Cup losses.
On this day in 2021, Chelsea became Champion league winners for the second time 💙🏆 pic.twitter.com/VePFh9V8By
— 🌹𝓐𝓴𝓾𝓪𝓱 𝓦𝓻𝓲𝓽𝓮𝓼🌹💙 (@akuahwritess) May 29, 2024
5. Jose Mourinho’s First Departure (2007)
Heartbreak isn’t always about a result on the pitch; sometimes it’s the end of an era. In September 2007, news broke that Jose Mourinho, the man who had delivered Chelsea’s first league title in 50 years, was leaving by mutual consent.
The connection between the “Special One” and the fans was visceral. He had transformed the club’s identity from “lovable losers” to arrogant winners. His exit followed a period of friction with the board, but for the fans, it felt like a death in the family.
José Mourinho motivating the Chelsea fans after a draw at the Emirates gave the league title to Man United back in 2007, which prevented Chelsea from 3-peating the Premier League.
Chelsea’s standards were always so high with him in charge.pic.twitter.com/B36FCUJ0cN
— IM🇵🇹 (@Iconic_Mourinho) March 2, 2023
The suddenness of the announcement, coming just after a disappointing draw against Rosenborg, left a void at the club that arguably wasn’t filled until his return years later.
