Pundits, journalists, and fans alike often talk about the ‘magic of the FA Cup‘. What exactly is it, however, that makes the FA Cup so special?
Is it the fact that the competition is the oldest in football’s history, even pre-dating the World Cup? Certainly. Is it because it remains one of the only free-to-watch domestic football tournaments on British television? Perhaps.
Or is it because its first major fixtures traditionally begin on the first weekend of the new year, when the spirit of Christmas still lingers in the air and grounds across the country are shrouded in a yuletide mist? Most definitely.
More than any of those things, however, the FA Cup is ‘magic’ because, more than in any other competition, it’s an opportunity for the underdogs to upset the big boys and pull off an infamous giant-killing.
Any club that is part of the English Football League system can partake in the FA Cup, meaning the likes of AFC Marine can end up playing Tottenham Hotspur, and Havant & Waterlooville can earn a trip to Anfield.
Marine and Havant weren’t able to pull off major upsets, but over the years, there have been plenty of others who have. So, with that in mind, here are our picks for the ten greatest-ever FA Cup upsets, ranked by shock value and importance.
10
Man City 0-1 Wigan, 2013
Manchester City weren’t quite the omnipotent footballing force they are today back in 2013, but Roberto Mancini’s squad was still full of world-class stars like David Silva, Yaya Toure and Sergio Aguero.
So when they faced relegation-threatened Wigan in the 2013 FA Cup final, only one outcome was expected. Instead, the Latics pulled off a remarkable upset, with midfielder Ben Watson scoring a 91st-minute winner for Roberto Martinez’s side in a historic 1-0 triumph.
Their celebrations didn’t last too long, though. Just three days later, Wigan were relegated from the Premier League after being thrashed 4-1 by Arsenal. They remain the only team to win the FA Cup and be relegated in the same season.
9
Liverpool 0-1 Wimbledon, 1988
The Crazy Gang beat the Culture Club
Liverpool were the most dominant side in English and European football in the 1980s. But in the 1988 FA Cup final, they came unstuck against Bobby Gould’s rough-and-ready Wimbledon side.
Dons midfielder Vinnie Jones set the tempo for the game early on, crashing into Steve McMahon in the opening minutes. From there, Gould’s team started chipping away at the Reds and got their reward in the 37th minute when midfielder Lawrie Sanchez headed home a Dennis Wise free-kick.
With an hour on the clock, Liverpool were given a lifeline in the form of a penalty. John Aldridge took it, but it was saved by Dave Beasant, and Wimbledon held on for the win.
At the final whistle, BBC commentator John Motson delivered the famous line: “The Crazy Gang have beaten the Culture Club.”
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8
Man Utd 0-1 Leeds, 2010
Brilliant Beckford bests Red Devils
Jermaine Beckford. Remember the name? Sir Alex Ferguson certainly will.
In January 2010, Manchester United, the reigning Premier League champions, hosted Leeds United at Old Trafford in the third round of the FA Cup. One of their biggest rivals, Leeds had sunk down to League One by this point, and as such, Ferguson’s side were expected to dismantle their visitors.
Beckford, however, had other ideas, with the Jamaica international scoring the only goal in a 1-0 win for Leeds, which left Ferguson fuming.
“I am shocked by the performance because our preparation for the game was very good. But we never got going,” the Scotsman said after. “We spoke about Beckford’s pace up front and we were caught napping.”
7
Wrexham 2-1 Arsenal, 1992
Red Dragons shock champions in gargantuan upset
Wrexham were rooted to the foot of the Fourth Division when they met Arsenal in the third round of the FA Cup.
It looked like it was going to be a routine win for the Gunners after Alan Smith put them in front, however a superb 25-yard free-kick from Mickey Thomas with 10 minutes to play left things in the balance.
Wrexham sensed blood and then pushed for the winner, which they got late, late on through Steve Watkin.
Not only was the win one of the biggest in Red Dragons’ history, but it also proved to be the catalyst in turning the club’s season around as they went on to escape relegation by finishing 14th in the league.
6
Shrewsbury 2-1 Everton, 2003
Toffees dumped out by fourth-tier Shrews
In January 2003, Third Division side Shrewsbury Town pulled off a huge upset as they beat Premier League high-flyers Everton 2-1 in the third round of the FA Cup.
Shrewsbury, who were managed by Everton’s most successful captain Kevin Ratcliffe at the time, took the lead through veteran Nigel Jemson, who curled in a superb free-kick from the edge of the box.
Substitute Niclas Alexandersson looked to have spared the Toffees’ blushes when he equalised on the hour mark, but Jemson then scored again with just a minute left to play, this time heading in Ian Woan’s free-kick at Richard Wright’s near post.
It was a joyous moment for the Shrews, but their season ended in dismay as they were relegated from the Football League.
5
Bournemouth 2-0 Man Utd, 1984
Harry Redknapp’s Cherries knock holders out
Prior to losing to Leeds in 2010, the last time Manchester United were beaten by lower-league opposition was by Bournemouth in the third round of the 1984 FA Cup.
On that day, a young Harry Redknapp was in charge at the Division Three side, who emerged as 2-0 victors against the previous year’s winners thanks to goals from Milton Graham and Ian Thompson.
In a report from the Evening Echo after the match, reporter Colin Smith wrote: “Bournemouth bubbled while United toiled – and were troubled. They say the Cup is a great leveller. But it was not the case this time, because the home side outclassed their opposition.”
4
Sunderland 1-0 Leeds, 1973
Revie’s men rolled over in finale upset
Sunderland were all the way down in Division Two when they faced all-conquering Leeds United in the 1973 FA Cup final.
In a turn of events that nobody saw coming, however, the Black Cats turned over Don Revie’s side, with a 32nd-minute goal from Ian Porterfield and a Gordon Banks-esque reflex save from goalkeeper Jim Montgomery enough to secure Sunderland their first FA Cup since 1937.
“I should pack it all in. there’ll never be another moment like it,” Sunderland boss Bob Stokoe said after the match.
3
Chelsea 2-4 Bradford, 2015
Bantams bite the Blues at Stamford Bridge
When Chelsea hosted Bradford City in the FA Cup fourth round at Stamford Bridge in January 2015, the Blues were top of the Premier League while the Bantams were in League One.
On the day, things started as expected, with the hosts soaring into a 2-0 lead within 38 minutes thanks to goals from Gary Cahill and Ramires.
Against all odds, however, Bradford then mounted an astonishing comeback, starting with a goal from former Premier League striker Jonathan Stead and ending with an added-time strike from Football League journeyman Mark Yeates.
To add insult to injury, former Chelsea academy star Filipe Morais was also on the scoresheet for the visitors.
2
Sutton United 2-1 Coventry, 1989
Super Sutton stun Sky Blues
In 1987, Coventry City won the FA Cup for the first time. Less than two years later, however, they were sent crashing out in the third round at the hands of a team four leagues below them.
Managed by Welshman Barrie Williams, Sutton United beat the Sky Blues 2-1 in front of 8,000 fans at Gander Green Lane, with Tony Rains and Matthew Hanlan scoring the vital goals.
One of the biggest upsets in FA Cup history, Williams said after: “The enormity of this result will reverberate throughout the whole of soccer.”
It wasn’t until 2013 that another non-league side beat a team from the top tier of English football, when Luton Town beat Norwich City 2-1.
1
Macclesfield 2-1 Crystal Palace, 2026
Delight for sixth-tier Silkmen
From one non-league shock to another. This is the biggest upset we have ever seen in the competition’s illustrious history.
In 2024/25, Crystal Palace surprised everyone when they won the FA Cup under Oliver Glasner. However, football can change quickly and as they attempted to defend their crown, were dumped out of the competition by sixth-tier Macclesfield in the third round during the 2025/26 campaign.
Once known as Macclesfield Town, they were competing in National League South at the time of this giant killing, making their remarkable 2-1 win over the Eagles even more impressive.
Managed by Wayne Rooney’s brother, John, Wazza fought back the tears post-game after seeing his sibling achieve the greatest accomplishment of his managerial career to date.
Paul Dawson’s fabulous first-half header opened the scoring for the hosts before Isaac Buckley-Ricketts shocked Palace further when he netted in the second period. Yeremy Pino gave the visitors hope by finding the net in the 90th minute but it was too little too late for the cup holders.
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