Sixth-tier Macclesfield produced possibly the biggest upset in FA Cup history after dumping out 2025 winners Crystal Palace in the third round.
Macclesfield became the first non-league side to beat the cup holders since 1908/09 - when, coincidentally, Palace themselves ended Wolves’ reign - thanks to a 2-1 victory at Leasing.com Stadium.
The Silkmen’s win was the latest giant-killing act in the competition’s history, and here we look at 10 of the most famous FA Cup shocks.
10 Famous FA Cup Shocks
Liverpool vs Wimbledon
Liverpool 0 Wimbledon 1 (1988, Final)
There have been plenty of upsets down the years, but perhaps none encapsulates the magic of the FA Cup more than the 1988 final.
Double-chasing Liverpool had been top dogs for much of the previous decade, winning European and domestic trophies aplenty and boasting household names such as John Barnes, Alan Hansen and Peter Beardsley, under the guidance of Kenny Dalglish.
Wimbledon had none of that. But what they did have was a style of play, infamous antics and a scant regard for reputation that would see the ‘Crazy Gang’ become a force of nature in English football. The highlight of that Dons era undoubtedly came in May 1988 at a stunned Wembley.
Lawrie Sanchez’s looping first-half header combined with Dave Beasant’s historic second-half penalty save from John Aldridge saw Bobby Gould's side record a giant-killing for the ages, with TV commentator John Motson declaring at the full-time whistle: ‘The Crazy Gang have beaten the Culture Club!’
Chelsea vs Bradford
Chelsea 2 Bradford 4 (2015, Fourth Round)
Chelsea boss Jose Mourinho warned ahead of the tie that it would be a “disgrace” for his Premier League pacesetters to be knocked out by League One Bradford. But that is exactly what happened as the Bantams staged one of the great FA Cup fightbacks at Stamford Bridge. All seemed to be going smoothly for the Blues as goals from Gary Cahill and Ramires saw them leading 2-0, but Jon Stead pulled one back just before the break to keep Bradford's hopes alive.
Filipe Morais then put the cat among the pigeons by equalising with 15 minutes to go, and Chelsea, despite Mourinho throwing on Eden Hazard, Willian and Cesc Fabregas to join Didier Drogba, Cesar Azpilicueta and co, then found themselves trailing when Andy Halliday struck with eight minutes left.
Bradford substitute Mark Yeates sealed victory in stoppage time as the Londoners - who would reach the final in 2017 and 2018 - were dumped out.
Wrexham vs Arsenal
Wrexham 2 Arsenal 1 (1992, Third Round)
Prior to Wrexham finding worldwide fame through their current Hollywood ownership, the most famous moment in their long history was almost certainly knocking Arsenal out of the 1992 FA Cup. The two clubs could hardly have been further apart on paper.
Arsenal were the reigning English champions, having lost just once en route to the 1990/91 title, while at the same time, Wrexham had only avoided falling out of the Football League due to a pre-planned competition expansion, the Welsh side finishing bottom of the Fourth Division. But it was the Red Dragons who roared to a remarkable victory at the Racecourse Ground thanks to late goals from captain Mickey Thomas and Steve Watkin.
Arsenal had taken a first-half lead through Alan Smith, but Wrexham drew level in the 82nd minute thanks to Thomas’ brilliant free-kick past England keeper David Seaman - one of the FA Cup’s most iconic moments - before Watkin’s winner two minutes later saw Brian Flynn’s men through.
Sutton vs Coventry
Sutton 2 Coventry 1 (1989, Third Round)
Coventry had produced an FA Cup upset of their own just 18 months previously when they beat highly-fancied Spurs 3-2 at Wembley to win the competition for the first - and only - time in their history, but the Sky Blues were on the receiving end in 1989. GM Vauxhall Conference side Sutton were five levels below Coventry but went ahead at a packed Gander Green Lane when left-back Tony Rains headed home from a flicked-on corner.
David Phillips drew Coventry level seven minutes into the second half with a low finish, but Sutton were not to be denied and retook the lead in the 59th minute following another well-worked corner routine. Mickey Stephens played the ball to the unmarked Phil Dawson on the edge of the box, and his first-time cross was volleyed home at the far post by Matthew Hanlan, making the bricklayer an instant FA Cup hero.
Sutton would go on to lose 8-0 to Norwich in the next round, but their place in legend was secure.
Norwich vs Luton
Norwich 0 Luton 1 (2013, Fourth Round)
It may not seem it now, with both Norwich and Luton having been around the top echelons of the English game in recent years, but the Hatters’ fourth-round win in 2013 was a considerable upset.
No non-league side had knocked out a top-flight club since Sutton shocked Coventry 24 years previously, but that’s precisely what Luton managed at Carrow Road. Luton were not your typical non-league club - they had been a Division One staple in the 1980s when they reached successive League Cup finals - but had fallen on hard times.
However, Paul Buckle’s outfit beat a Norwich side that included a young on-loan Harry Kane 1-0, thanks to substitute Scott Rendell’s late winner, becoming only the seventh non-league team to reach the FA Cup fifth round since World War Two.
Hereford vs Newcastle
Hereford 2 Newcastle 1 (1972, Third-Round Replay)
Watch any FA Cup highlights package, and you are sure to see the Ronnie Radford thunderbolt and subsequent celebrations that helped Hereford create a record-breaking upset against Newcastle.
Malcolm Macdonald’s 82nd-minute goal finally appeared to have ended Hereford’s brave challenge on an Edgar Street mudbath, but Radford had other ideas. Winning the ball midway inside Newcastle’s half, Radford played a one-two with Brian Owen before letting fly from 30 yards with a thunderbolt that flew into Willie McFaul’s top corner.
Radford wheeled away, both arms stretched to the sky and hitching up his white number 11 shirt, which suddenly seemed too small for him, before being mobbed by team-mates and scores of jubilant home fans who had raced onto the pitch. Hereford were not done yet, though, and substitute Ricky George netted an extra-time winner as the fifth-tier Bulls became the lowest-ranked team to beat a top-flight club.
Wigan vs Man City
Wigan 1 Man City 0 (2013, Final)
True upsets in FA Cup finals are few and far between, but Wigan’s win over Man City is in that category. Both teams were in the Premier League, but newly-minted City were already establishing a dynasty that would go on to dominate English football, while Wigan were destined for imminent relegation to the Championship.
Roberto Mancini’s City starting XI was a who’s who of global superstars, among them Sergio Aguero, Carlos Tevez, Yaya Toure, David Silva and Vincent Kompany, but it would be Wigan substitute Ben Watson who would snatch the limelight with a stoppage-time winner. The 27-year-old had barely been on the pitch for 10 minutes when he met Shaun Maloney’s inswinging corner at the near post to send a glancing header past Joe Hart, securing the Latics their maiden FA Cup crown.
Three days later, Wigan lost 4-1 at Arsenal to become the first team to be relegated from the top division in the same year as lifting the FA Cup - they have not returned to the Premier League since. The 2013 final proved to be Mancini's final game in charge of City, with the Italian, who had seen defender Pablo Zabaleta sent off in the 84th minute at Wembley, sacked by City and replaced by Manuel Pellegrini.
West Brom vs Woking
West Brom 2 Woking 4 (1991, Third Round)
Tim Buzaglo was the name on everybody’s lips in January 1991 after netting a blistering second-half hat-trick to help non-league Woking dump out Second Division West Brom. Colin West’s header had given West Brom a half-time lead at the Hawthorns, but Buzaglo turned the tie on its head in the space of 15 second-half minutes.
The 29-year-old, who had also played international cricket for Gibraltar, twice broke through the heart of the West Brom defence to put Woking 2-1 ahead before drilling home at the far post to complete his treble. Substitute Terry Worsfold headed home a fourth for the part-timers, and although the beleaguered Baggies pulled one back, it was too little too late to avoid a shock exit or save manager Brian Talbot’s job.
In 2022, a University of Bath mathematical study commissioned by the Football Association ranked Woking’s result against West Brom as comfortably the least likely FA Cup third-round outcome in the last 50 years, at odds of almost 16 million to one.
Sunderland vs Leeds
Sunderland 0 Leeds 1 (1973, Final)
Before Wimbledon and Wigan, there came Sunderland. Leeds were overwhelming favourites to defend their FA Cup crown in 1973 after coming up against unfancied Sunderland in the only final to be played using an orange ball.
Don Revie's 'Mighty Whites' were one of the top teams in Europe with a trophy cabinet overflowing with spoils from previous years and in the midst of a run which would see them finish in the top four of the First Division for 11 successive seasons. Sunderland, meanwhile, were down in Division Two and had reached the FA Cup final after being taken to replays in each of the opening three rounds.
But Bob Stokoe’s underdogs caused one of the competition’s biggest upsets thanks to Ian Porterfield's first-half strike and goalkeeper Jim Montgomery’s heroics, helping Sunderland win what would prove to be their last major trophy for almost 50 years.
Macclesfield 2 Crystal Palace 1 (2026, Third Round)
Palace had achieved their own fairytale by winning the FA Cup for the first time last year, but the Eagles were brought crashing back to earth in the opening match of their defence.
Macclesfield were 118 places below their Premier League visitors in the pyramid, yet the National League North side drew first blood when captain Paul Dawson headed home a free-kick just before half-time.
Isaac Buckley-Ricketts made it 2-0 in the 60th minute following a goalmouth scramble, and Palace, whose much-changed side still included England duo Marc Guehi and Adam Wharton, could only pull a late goal back through Yeremy Pino’s free-kick.
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