When the referee finally blew for full time following Manchester City’s 1-1 draw with Bournemouth on May 19, 2026, it marked the end of the banter era for Arsenal, who ended a 22-year wait for the English Premier League title.
While the Gunners are on course to be labeled “undeniable” if they end up breaking their UEFA Champions League duck on May 30, their success was not built overnight.
It was forged in the fires of immense adversity, public ridicule, and ruthless internal decisions. Before the club could lift the trophy, they had to systematically tear themselves down and survive a series of agonizingly low points.
For Striver.Football, we look back at the 10 most painful, defining moments of heartbreak, sacrifice, and dark days that Arsenal had to endure between 2005 and 2025 on their long, winding road back to the top.
10. The 2006 Champions League Final Heartbreak
In May 2006, Arsenal stood mere minutes away from immortality. Despite Jens Lehmann’s early red card, Sol Cambell’s header put the Gunners into the lead during their Champions League final against Barcelona in Paris.
However, two late, agonizing strikes from Barcelona shattered the dream at Saint-Denis Stadium, marking the definitive end of the "Invincibles" era and beginning a long, painful transition period.
With the Gunners set to move to the Emirates Stadium, they were denied a glorious chance to bring that shiny trophy into their new arena.
9. Eduardo’s Horrific Injury and Arsenal’s 2007/08 Collapse
The 2007/2008 season is arguably the closest Arsenal ever got to winning their first league trophy of the Emirates era.
In February 2008, Arsene Wenger's young, breathtakingly fluid side sat five points clear at the top of the league.
They travelled to Birmingham City, but something horrific happened: on-form striker Eduardo da Silva suffered a year-long leg break, followed by a late penalty equaliser and captain William Gallas’s infamous, tearful breakdown on the pitch.
It was a moment that completely broke the squad’s psychological resolve. A string of draws saw the title slip away.
8. The Painful Era of Losing Captains and Superstars
From 2007 up until 2018, Arsenal transformed from a title-winning machine into a finishing school for Europe's elite.
Fans had to endure the excruciating pain of watching their absolute best players force exits to direct rivals. From Cesc Fabregas deserting to Barcelona, to Samir Nasri jumping to Manchester City, before the ultimate final nail in the coffin: captain Robin van Persie moving to Manchester United in 2012 to single-handedly win them the league.
Although the club stabilized in 2013 by starting to sign established stars like Mesut Ozil, in 2018, the club still had to let go of Alexis Sanchez to Manchester United, much to the anger of the fans.
7. The 8-2 Humiliation at Old Trafford (August 2011)
This was the absolute rock bottom of the Arsene Wenger era. Depleted by injuries and the high-profile departures of Fabregas and Nasri, a makeshift Arsenal side was utterly dismantled and humiliated 8-2 by Manchester United.
It was a day of unparalleled footballing ridicule that exposed the club's structural fragility on a global stage, forcing a frantic, reactionary trolley-dash on transfer deadline day.
Among the five signings they bought was a certain Mikel Arteta from Everton, with Wenger desperately needing some injection of experience and leadership to stabilise the unit.
6. The 2015/16 Leicester City Anomaly
In a season where Man City, Chelsea, Liverpool and Man United were struggling, the Premier League title was Arsenal’s to take.
Famously, Danny Welbeck’s 95th-minute winner against Leicester City at the Emirates in February sent fans into a frenzy, believing the title was destined for N5.
Instead, a catastrophic failure to beat lower-half teams saw Claudio Ranieri’s Leicester complete a fairytale, leaving Arsenal as the ultimate punchline. It was a failure that coincided with the start of protests by angry fans calling for “change”.
5. Arsenal’s Toxic Club Culture in 2019
After 22 years, Arsene Wenger left in 2018, with the club appointing Unai Emery. With American billionaire Stan Kroenke finally buying out Alisher Usmanov’s stake and then beginning the process of privatising the club, there was an enormous 18 months of trials and errors, which resulted in an identity loss
Although Emery took the club to within one point of Champions League qualification and a Europa League final - embarrassingly losing 4-1 to Chelsea in the process, he was sacked in November 2019.
Mikel Arteta was then appointed as coach just four days after incidentally sitting on the opposite bench inside a half-empty Emirates stadium as a Kevin De Bruyne-inspired Man City dismantled the club 3-0.
He instantly commissioned a comprehensive three-month internal survey of the club's staff.
When the feedback was compiled into a word cloud to describe the atmosphere at Arsenal, a single, dominant word stared back at him: "Toxic."
4. The 5-0 Manchester City Drubbing and Dead Last (August 2021)
The lowest on-field moment of the early Arteta rebuild. Arsenal lost their opening three Premier League games of the 2021/22 season without scoring a single goal.
The misery culminated in a 5-0 thrashing at the hands of Manchester City at the Etihad, leaving Arsenal dead last in the Premier League table.
External mockery reached a fever pitch, testing the board's conviction to its absolute limits. It was a season that was exclusively covered by Amazon, who produced a behind-the-scenes season review of the club as part of their All or Nothing series, which gave the fans an insight into Mikel Arteta’s “process”.
3. The Agonizing 2022 Champions League Collapse to Spurs
In May 2022, Arsenal had a top-four finish completely in their hands. A win against bitter rivals Tottenham Hotspur would have sealed Champions League football ahead of schedule.
Instead, they collapsed to a 3-0 North London Derby defeat. Spurs snatched the final Champions League spot, subjecting Arsenal to another year of Europa League Thursday nights.
They went on to lose 2-0 to a Newcastle United side rejuvenated by their Saudi Arabia Public Investment Fund injection, forcing them to settle for the Europa League.
2. Arsenal’s 2023 Title Collapse and the 11-Day Meltdown
After leading the Premier League for the vast majority of the 2022/23 season by playing a brand of exciting, attacking football, the pressure of the chase caught up with a young squad.
Having already been hit hard by a season-ending injury to influential center back William Saliba, Arsenal surrendered consecutive 2-0 leads to draw 2-2 with Liverpool and West Ham, followed by a panicked 3-3 draw at home to bottom-placed Southampton.
A subsequent 4-1 mauling by Manchester City and then a 1-0 loss to Nottingham Forest away effectively handed Pep Guardiola the trophy.
Honorable Mentions
Over that period, the club has endured some more painful moments. One might remember Abou Diaby’s ankle injury against Sunderland, which effectively relegated a player many considered the new Patrick Vieira to constant stop-start moments in his career.
You might even remember the 2013/14 season, another where Arsenal led for a majority of the season before capitulating in March. There are also the 10-2 thrashings to Bayern Munich on aggregate in 2017.
There are also the Champions League semi-final losses to Man United and PSG in 2009 and 2024 respectively. But none of them hit Arsenal as hard as the ultimate number one point:
1. The Three Consecutive Second-Place Heartbreaks (2023-2025)
You do not finish second three times in a row without developing deep psychological scars.
Between 2023 and 2025, Arsenal went toe-to-toe with Manchester City, pushing them to the absolute limit, only to fall agonizingly short at the final hurdle every single year.
The footballing media repeatedly slapped them with the "perennial bridesmaids" tag, doubting whether this group possessed the ruthless edge required to actually win a trophy. Guess what? They finally did it in 2025/2026.
Arsenal Finally Escaped the Banter Era
Every single one of those heartbreaks were a necessary brick during the 22 years Arsenal tried to recapture their lost glory days.
Although it has taken practically a quarter of a lifetime, they eventually stripped away the softness that plagued North London for two decades and replaced it with an iron-willed resilience.
The club also showed they finally are not title bottlers. The jokes can stop. Arsenal are now the standard measure, and the club might just be getting started.
