In recent years, being an Arsenal fan means testing your physical, social, and mental resolve.
Supporting any football club means you’ve signed up to lifetime of allowing 11 men to decide if you’ll have a good weekend or not. However, with Arsenal, it’s different. It comes with extra levels of chaos that has seen Arsenal fans ask if the universe is against them.
The Gunners have witnessed some very depressing moments in their history that have made them even lose some fans. They have gone from being one of the top clubs in London to being one of the most bantered clubs in the world.
This article discusses some of the most heartbreaking moments in Arsenal’s history that has caused them to be heavily bantered.
1. 2006 Champions League Final
This remains the ultimate “what if” in the club’s history.
Playing in their first-ever Champions League final, Arsenal looked like a team of destiny. Even after goalkeeper Jens Lehmann was sent off in the 18th minute, the first-ever red card in a UCL final, the ten-man Gunners took the lead through a towering Sol Campbell header.
For 76 minutes, Arsenal defended like warriors. Thierry Henry had a golden chance to make it 2-0 and seal immortality, but Victor Valdes made the save of his life. Minutes later, the rain in Paris turned cold. Samuel Eto’o equalized, and to completely end their dreams, Juliano Belletti’s shot squeezed through Manuel Almunia’s legs to break Arsenal’s hearts.
#OnThisDay in ’06 @FCBarcelona came from behind to win the #UCLfinal 2-1 vs @Arsenal. It was their first in 14yrs 🏆 pic.twitter.com/TPMC4b6Egq
— FIFA (@FIFAcom) May 17, 2016
To be 14 minutes away from being Kings of Europe with ten men, only to lose it all, is a scar that hasn’t fully healed.
2. The 2011 League Cup Final vs Birmingham
By 2011, Arsenal had gone six years without a trophy. A League Cup final against a struggling Birmingham City side was supposed to be the “easy” way to end the drought and kickstart a new era. Instead, it became the punchline of a very cruel joke.
✨ 13 YEARS AGO TODAY… 🏆🔵
Birmingham City win League Cup final against Arsenal courtesy of last-minute winner from Obafemi Martins! 🇳🇬 pic.twitter.com/mvEhaCTtIN
— EuroFoot (@eurofootcom) February 27, 2024
With the game tied at 1-1 in the 89th minute, a simple long ball caused a catastrophic lack of communication between Laurent Koscielny and goalkeeper Wojciech Szczęsny. The ball bobbled out of their grasp and into the path of Obafemi Martins, who tapped it into an empty net. The sight of the Arsenal players slumped on the turf while Birmingham celebrated remains the quintessential image of the “banter era.”
3. The Humiliating 8-2 Loss at Old Trafford
If the League Cup final was a heartbreak of disappointment, the 8-2 defeat to Manchester United was a heartbreak of pure humiliation. Arsenal traveled to Old Trafford with a depleted squad, but no one expected a capitulation of this magnitude.
Wayne Rooney netted a hat-trick as United scored at will against a shell-shocked Arsenal defense. It wasn’t just the scoreline; it was the realization of how far the club had fallen from the heights of the early 2000s. It was the heaviest defeat Arsène Wenger ever suffered, and it forced a panicked, last-minute transfer spree that changed the club’s recruitment strategy for years.
📆 #OnThisDay eight years ago, Manchester United beat Arsenal 8-2 at Old Trafford 😳pic.twitter.com/hwHO39eWja
— GOAL (@goal) August 28, 2019
4. The 1,000th Game Nightmare (2014 6-0 Loss to Chelsea)
This one feels more like a humiliation for Wenger, but Arsenal also shared in the shame, and they won’t forget it, not in a million years.
Arsène Wenger’s 1,000th game in charge of Arsenal was supposed to be a celebration of a legendary career. Instead, José Mourinho, Wenger’s ultimate nemesis, turned it into a funeral.
Jose Mourinho beat Wenger in his 500th game as Arsenal boss, gave him 9 years to prepare, called him a “specialist in failure,” then thrashed him 6–0 in his 1000th game, and even left early to tell his wife the score.
Absolute shithousery 🤣pic.twitter.com/Hv4eotmN03 https://t.co/hCebXvoJwp
— Rado 🎈 (@thee_ovie) November 15, 2025
Within 17 minutes, Arsenal were 3-0 down and a man down. In a bizarre moment of “Peak Arsenal,” referee Andre Marriner sent off Kieran Gibbs for a handball committed by Alex Oxlade-Chamberlain. The tactical and disciplinary collapse was total.
Losing 6-0 on such a milestone day felt like a personal insult to Wenger’s legacy and served as a brutal reminder of the gap between Arsenal and the league’s elite at that time.
5. The “Triple Bottling” Era (2022–2025)
Perhaps the most painful of all are the recent years, because Arsenal were actually good again.
After years of mid-table mediocrity, Mikel Arteta turned the Gunners into title contenders, only for the finish line to prove elusive three times in a row.
In the 2022/23 season, Arsenal led the table for 248 days, an English top-flight record for a team that didn’t win the league. The William Saliba injury triggered a collapse that saw a healthy lead evaporate under the Manchester City machine.
Arsenal really blew a staggering 19 (yes NINETEEN!!!) point lead to bottle the league. 😂😂😂 goodnight.
— Hotspur Edition (@HotspurEdition) April 26, 2023
In the 2023/24 season, fans couldn’t even believe their eyes. Once again, the Gunners dominated the league and showed they were title contenders,
BIGGEST bottle job in the history of football, belongs to the ARSE. 🫵🏻😂
98% on top, lost a team who was on top for 2 weeks. 😭😭😭😭😭😭😭😭😭😭 pic.twitter.com/r7dsnyp9Ep
— F Ø Ø T B Λ L L _ Λ Ð Ξ P T 🏆🐦🔥💫 (@Football_Adept) February 8, 2025
but by the end of the season, that’s al they were, contenders.
A near-perfect run in 2024 was ruined by a single 2-0 home loss to Aston Villa. Despite finishing on 89 points, they lost the title by just two points.
The 2024/25 season increased the level of banter Arsenal received. They once again contended for the title but were washed away by the brilliance of a Liverpool side who were dogged in the pursuit. The “three-peat” of disappointment was completed as late-season draws again allowed the title to slip away.
At the end of that season, they had finished second in the Premier League three times in a row. To be so close to the pinnacle for three straight years and come away empty-handed has created a unique kind of sporting trauma.
This trauma may not be over, as Arsenal have once again shown signs of slipping. They are just five points ahead of rivals Manchester City with a game in hand. Should City win their game in hand, the gap will be reduced to two points, meaning Arsenal have lost a 12-point lead which they once had at the beginning of the season.
The Premier League title race is still on, but should Arsenal bottle again, this could possibly be their most heartbreaking moment ever.
