FA Cup upsets are synonymous with English football. The world’s oldest cup competition has always been English football’s great leveller, a competition where history, money and reputation mean absolutely nothing the moment the whistle blows. It’s the one place where a Premier League giant can rock up with a £300m squad, only to be bullied, rattled and dumped out by a team whose entire wage bill wouldn’t cover their left‑back’s weekly salary.
And that’s the magic. The chaos. The reason we keep coming back.
But not all giant‑killings are created equal. Some are cute little upsets. Others are seismic cultural moments that shake the sport to its core. And in the modern era, with the financial gulf bigger than ever, the truly outrageous ones feel even more impossible.
So here it is: the definitive, no‑nonsense, nostalgia‑drenched ranking of the Top 10 FA Cup Upsets of All Time, weighted for context, stakes, shock factor and the sheer audacity of the underdog.
Let’s get stuck in.
10. Hereford 2–1 Newcastle (1972)
The OG giant‑killing. The one your dad still bangs on about. The pitch looked like a cow field, the ball bounced like a brick, and Ronnie Radford’s 30‑yard thunderbolt is still replayed every January as if it happened yesterday.
Newcastle were a proper First Division side. Hereford were non‑league part‑timers. The gulf was enormous, even in the pre‑money era, and yet Hereford didn’t just hang on; they won it with one of the most iconic goals in FA Cup history.
It’s not the biggest upset on this list, but it’s the blueprint. The original chaos merchant.
9. Sutton United 2–1 Coventry City (1989)
Coventry weren’t just a top‑flight team, they were the reigning FA Cup holders. Sutton were non‑league. This should have been a routine 4–0 away win, a nice day out for the locals, and nothing more.
Instead, Sutton produced one of the most famous shocks ever seen in the competition. The image of their players celebrating in that tiny, packed ground is pure FA Cup nostalgia. Coventry were stunned. The country was stunned. And Sutton became immortal.
If this happened today, it would break the internet.
8. Wrexham 2–1 Arsenal (1992)
Funnily enough, this wasn’t even a time when Arsenal bottled it. The Gunners were the reigning champions of England. Wrexham were bottom of the entire Football League the season before. The gap between the two clubs was absurd.
But the FA Cup doesn’t care about gaps.
Mickey Thomas, 38 years old, built like a geography teacher, smashed in a free‑kick that still lives rent‑free in Arsenal nightmares. Then Steve Watkin completed the turnaround, and the Racecourse erupted.
This wasn’t just an upset. It was a football miracle.
7. Oldham 3–2 Liverpool (2013)
Oldham were a League One side fighting relegation. Liverpool had Luis Suárez, Daniel Sturridge, Steven Gerrard and a squad worth more than Oldham’s entire club.
But on that day, Matt Smith turned into peak Didier Drogba. He bullied Liverpool’s defence, scored twice, and dragged Oldham into FA Cup folklore.
This is one of those modern upsets that feels even bigger in hindsight. The physicality, the chaos, the disbelief, it was everything the FA Cup is supposed to be.
6. Macclesfield 2-1 Crystal Palace (2026)
A few weeks ago, this happened, and it still doesn’t feel real.
Macclesfield, a non‑league club rebuilt from the ashes only a few years earlier, hosted FA Cup holders Crystal Palace. A side with international players, elite facilities and a budget that dwarfs anything outside the top two divisions.
And Macclesfield beat them. Deservedly. In 2026. In the era of sports science, data departments and squads worth hundreds of millions.
This is exactly why modern giant‑killings hit harder. The gulf is enormous, and yet Macclesfield bridged it with belief, organisation and pure FA Cup mayhem.
5. Wimbledon 1–0 Liverpool (1988)
This is where history meets mythology.
Liverpool weren’t just good, they were the best team in the country for a decade. A machine. A dynasty. A club that dominated English football with style, swagger and inevitability.
Wimbledon were the opposite. The Crazy Gang. Misfits. Outcasts. A team built on chaos, intimidation and sheer bloody-mindedness.
And yet, on the biggest stage of all, they beat Liverpool in the FA Cup Final. Lawrie Sanchez scored, Dave Beasant saved a penalty, and the football world watched in disbelief as the ultimate underdogs toppled the ultimate giants.
It wasn’t just an upset. It was a cultural moment. A story that still defines the FA Cup
4. Manchester City 0–1 Wigan Athletic (2013)
A relegated Wigan side beating Manchester City, the richest squad in England, in the FA Cup Final.
Read that again.
This wasn’t a rotated City XI in the third round. This was Wembley. Full strength. Full stakes. Full expectation.
And yet Wigan, who would be relegated days later, produced one of the most astonishing results in modern football. Ben Watson’s header is the stuff of legend. The fact it happened in a final makes it even more outrageous.
If you wrote this in a script, you’d be laughed out of the room. The best of all the FA Cup upsets that took place in a final.
3. Plymouth Argyle 1–0 Liverpool (2025)
This one is still fresh, and it’s already one of the FA Cup classics.
Plymouth were a Championship‑level side with a modest budget and a squad built on smart recruitment rather than star power. Liverpool were one of the best teams in Europe, and would go on to win the Premier League that same season.
That context makes this result enormous. Liverpool weren’t in transition. They weren’t rotating heavily. They weren’t off the boil. They were elite. And Plymouth beat them, clean, deserved and without fluke.
In the modern era, with the financial gulf at its widest, this is one of the most remarkable giant‑killings ever.
2. Manchester United 0–1 Leeds United (2010)
This one still feels impossible.
Leeds were in League One. Not the Championship. League One. Two divisions below Manchester United, who were Premier League champions and Champions League finalists.
And yet Leeds went to Old Trafford, the fortress, the theatre, the place where underdogs go to die, and won.
Jermaine Beckford’s goal is etched into FA Cup history. The shockwaves were enormous. This wasn’t just a cupset; it was a humiliation for United and a moment of pure catharsis for Leeds fans.
In terms of scale, context and sheer disbelief, it’s right near the top.
1. Chelsea 2–4 Bradford City (2015)
The greatest of all the FA Cup upsets.
Chelsea were 2–0 up at Stamford Bridge. Mourinho was in full “nobody beats us here” mode. The squad was stacked with world‑class players. This should have been a routine demolition.
Instead, Bradford, a League One side, scored four. Not one. Not two. Four. At Stamford Bridge. Against a title‑winning Chelsea side. After being 2–0 down.
It’s the perfect FA Cup shock: scale, stakes, narrative, disbelief, and the kind of chaos that makes you question whether football is even real.
Nothing tops it.
Conclusion: The FA Cup Will Always Be Mayhem
The beauty of the FA Cup is that it refuses to be predictable. Money, status, reputation, none of it matters when a lower‑league side smells blood. The competition has survived every attempt to modernise, sanitise or commercialise it because it thrives on moments like these.
Moments where the impossible becomes inevitable. Moments where giants fall. Moments where football reminds you why you fell in love with it in the first place.
And as long as the FA Cup exists, there will always be another upset waiting around the corner, another Plymouth, another Wigan, another Wimbledon.
Because in this competition, chaos isn’t the exception. It’s the rule.
