
The FA Cup is arguably the most prestigious cup you can win in English Football, with hundreds of teams fighting for that singular spot as champion. The competition is loved by all for its ability to pull off shock results you did not think were possible; everyone can beat anyone; there are no guarantees.
On Saturday, we saw arguably the biggest upset in the competition's 155-year history as non-league Macclesfield FC beat the reigning champions Crystal Palace. The day will be remembered by all those in the town of Macclesfield and put to the back of the memory by all those travelling Palace fans.
The result reminded us why we love the FA Cup. We thought we'd take a trip down memory lane. Here are the 10 biggest upsets in FA Cup history!
We start this historic list with a long trip back to 2025... Premier League leaders Liverpool were stunned by a Plymouth Argyle side that went on to finish 23rd in the Championship. The game was one of the biggest shocks we'd seen in years, with the Reds losing just three times prior to this result. It was Slot's first year in charge at Merseyside, and he was shown what the true magic of the FA Cup looked like.
So what happened in the game? Well, a boring first half saw just one shot on target, that a long-range effort from James McConnell. Plymouth came firing in the second half as Ryan Hardie converted from the spot just eight minutes after the restart. The away side then piled on the pressure but found no way through, ending any hopes they had of winning the Quadruple.
PLYMOUTH HAVE KNOCKED LIVERPOOL OUT OF THE FA CUP!!!!!! 🏆⚽️
— Match of the Day (@BBCMOTD) February 9, 2025
Bottom of the Championship 1-0 Top of the Premier League.#FACup pic.twitter.com/JQ9TAQi70d
David Moyes is one of the most underrated managers in recent years, making West Ham European Champions and taking Everton to a fourth-place finish in 2005. However, a day he'll want to forget came back in 2003 when his Everton side, which included a young Wayne Rooney, fell short to the Shrewsbury side that sat 80 places below them.
Everton's loss was not a shock if you watched the game; they were dominated from minute one and played off the park by Shrewsbury hero Nigel Jemson. Shrewsbury's 34-year-old captain opened the scoring with a stunning free kick and later on retook the lead with a header that would send his side into the fourth round.
The Cherries had one of the most historic days in existence, as young Harry Redknapp's side beat the reigning FA Cup champions, Manchester United. Ron Atkinson led the Red Devils at the time and had the likes of Bryan Robson in their ranks. Yet it was the Third Division side that progressed to the fourth round in a huge upset.
The game was huge for the town of Bournemouth, with everyone taking to the streets to support. This even delayed Bournemouth's team coach arriving at Dean Court, with the roads being so full. Goals from Milton Graham and Ian Thompson secured a 2-0 win for the Cherries and put Harry Redknapp's name on the map.
Liverpool make the list for the second time already as they crashed out in the FA Cup fourth round. An Oldham side that sat in League One at the time upset the Premier League giants, with an impressive brace from the big man Matt Smith.
This Liverpool side was not short of superstars, with Luis Suarez, Raheem Sterling and Daniel Sturridge all starting. The home side took the lead through Matt Smith, who doubled his tally to make it 2-1. Reece Wabara then netted a back-post header to extend their lead, before a Joe Allen volley found the net to worry the home side. Oldham managed to see the game out, progressing to the fifth round.
𝗙𝗔 𝗖𝗨𝗣 𝗨𝗣𝗦𝗘𝗧𝗦 🥲
— Betmate (@betmate_app) January 4, 2024
The third round of the #FACup starts tonight!
Let’s take a look back at some Cup upsets 👀👇
🗓️ Jan 2013
🔵 Oldham 3-2 Liverpool 🔴
Matt Smith at the double & Reece Wabara with a magnificent header sealed the win 🔥pic.twitter.com/sLERAtAt7E
2011 marked Stevenage's first season in the Football League, a historic year in itself. But what made it even better was their FA Cup run that saw them beat the famous Newcastle United. The Magpies finished 12th in their first season back in the Premier League, but Pardew's side would become just the fourth team since the formation of the Premier League to lose to a fourth-division side.
The 'Boro' dominated the fixture, enjoying more of the ball than the visitors. Stacy Long's deflected strike gave Stevenage the lead, before Michael Bostwick gave them a two-goal lead. Cheick Tioté saw red before X's most hated man, Joey Barton, pulled one back for Newcastle. Peter Winn secured a historic win for the League Two side, sending them through to the fourth round. 2011, a year to remember for Stevenage.
A Chelsea side that had just reached the semi-final of the Champions League the year before welcomed a League Two Bradford City to Stamford Bridge. The game is one that most modern football fans remember, as the team ranked 49 places below scored an impressive four goals on a day that went down in their history.
The home side took a 2-0 lead and looked set to cruise to victory before Jon Stead pulled one back, and then Filipe Morais found an equaliser. Bradford had done the unthinkable, pulling level, but didn't stop there, completing the most amazing comeback as Andy Halliday and Mark Yeats completed the upset. This Chelsea side went on to win the Premier League this year, while Bradford finished 7th in League Two. Their fairytale story would end in the next round with a defeat to Reading.
ON THIS DAY 2015: Bradford City 4-2 win at Chelsea #BCAFC #BANTAMS pic.twitter.com/7BDVcAbJf5
— FootballAwaydays (@Awaydays23) January 24, 2024
Arsenal were the reigning First Division Champions and travelled to the Racecourse in the FA Cup third round. This Wrexham side played in the Fourth Division, where they finished bottom in the previous year. The Gunners took the lead, much to the disappointment of the crowd, with Alan Smith converting a header from a Paul Merson cross.
The game approached its final minutes when Mickey Thomas equalised through a free kick in the 82nd minute. It was a quick double blow for Arsenal, as just two minutes later, the home side went ahead after Steve Watkin put it past David Seaman. The game ended and was met by a pitch invasion that saw all fans and players celebrate together. Wrexham were rewarded with another big tie as they faced West Ham in the next round. The run stopped there as they lost in a replay at the racecourse.
Lincoln wrote their name in the history books this day, becoming the first non-league side to reach the FA Cup quarter-finals of the FA Cup in a century. Their whole FA Cup run is one that deserves praise, as they beat Oldham, Ipswich and Brighton along the way. The most memorable game was the away win at Turf Moor.
The non-league side came out 1-0 victorious thanks to an 89th-minute winner from Raggett; this was their only shot on target in the entire game. The support was immense, with over 3000 travelling away fans. Unfortunately, their run came to an end in the quarter-finals as they were thumped 5-0 at the Emirates by Arsenal.
Was this the greatest FA Cup run of all time?
The oldest of our FA Cup upsets comes from back in 1972 when top-flight Newcastle United lost to a non-league Hereford. The fixture was a replay after Hereford United picked up a 2-2 draw at the famous St James's Park. This draw was an impressive feat in itself, but Hereford did not stop there...
The replay has one of the most dramatic endings you will ever see. Newcastle took a late 2-1 lead before Ronnie Radford popped up with one of the most famous goals in FA Cup history, a 30-yard screamer. This took the game to extra time, where the non-league side scored the winner. The goal came from substitute Ricky George, who wrote his name in FA Cup glory for eternity. The result was one not seen in years, as Hereford became the first non-league club to defeat a First Division side since 1949.
The biggest upset of them all is the most recent. It comes in the form of the National League North (6th tier). Macclesfield defeated the reigning champions, Crystal Palace, in a game that they dominated throughout. Just the 117 places separated the two sides in the football pyramid, and most gave the home side no chance at victory, including me, but Palace started slowly and were punished by an outstanding header from captain Paul Dawson, who went on to win Man of the Match.
The Eagles tried their hardest to get back in the game, but having the likes of Borna Sosa on the pitch made that near impossible. The LB looked so out of place; he wouldn't even get into the Macclesfield side. Oliver Glasner, who has been linked with a move to Manchester United, made some very questionable changes, and within 15 minutes of the restart Buckley-Ricketts had doubled the non-league side's lead. Yeremey Pino, who has been extremely disappointing in a Palace shirt, got a late goal back for the Eagles, but it proved too little too late as the game ended 2-1.
After the best days of my life back in May, my high-flying Eagles have been shot down and are yet again back to ruining my weekends. So the day was historic for most, but one to forget for me and the rest of us Palace fans.
FA Cup holders Crystal Palace crash out after losing 2-1 to 6th-tier Macclesfield FC, the lowest-ranked team left in the tournament.
— B/R Football (@brfootball) January 10, 2026
It’s the first time since 1909 the holders have been knocked out by a non-league side.
SIMPLY. HEROIC.
✨🤯 pic.twitter.com/haDE7jMQNT
Join our newsletter
Become a part of our community and never miss an update from Football Park.
Contact Sales