The magic of the FA Cup is never personified more than when an FA Cup upset hits and here we take a look at the greatest FA Cup upsets of all time, in no particular order.
Biggest FA Cup Shocks in History
Biggest FA Cup shocks of all time
Sutton 2-1 Coventry -1989
Starting in no particular order, we have Sutton United who triumphed over the current holders of the FA Cup in 1989, Coventry. Indeed, the high-flying top flight side had beaten Tottenham Hotspur just 18 months prior to meeting the non-league Sutton, who were boasting not a single full-time employee in their squad, as Tony Rains and Matthew Hanlan scored for the English teacher Barrie Williams' side.
This was is FA Cup magic in a nutshell; a non-league outfit whose two goalscorers became instant celebrities appeared on Terry Wogan the following Monday.
Liverpool 0-1 Wimbledon - 1988
Arguably the most famous cup final in English football history and without question the most famous story in FA Cup history, as The Crazy Gang triumph against all the odds to beat the favourites and the league champions Liverpool at Wembley.
That day, Wimbledon keeper Dave Beasant became the first keeper in history to save a penalty in the FA Cup final, before a Dennis Wise free kick was headed home by Lawrie Sanchez, as the London outfit scrapped for every ball and fought for every tackle.
A truly unforgettable moment in British sporting history and one of the greatest FA Cup triumphs we've ever witnessed.
Arsenal 0-2 Millwall - 1995
Arsenal, the 14-time champions of the FA Cup, have had their share of both FA Cup upsets and triumphs over the very best, most recently as they beat Manchester City and Chelsea in 2020 to lift the trophy.
However, back in 1995, George Graham's side who held the European Cup Winners' Cup and won the FA Cup three years prior, lost to Millwall in a replay at Highbury.
Not many teams went to Highbury and got a result and barely anybody got past Arsenal in the 90s in the FA Cup, but this fearless Millwall side did so with relative ease in north London.
Manchester City 0-1 Wigan Athletic - 2013
Manchester City were one of the shortest odds in recent times in the 2013 FA Cup final (4/11), as Roberto Mancini's men comfortably finished second in the league, a year after they had won the Premier League for the first time ever.
At the same time, Wigan Athletic were just days away from being officially relegated to the Championship and needed to win at the Emirates just three days after the FA Cup final, where they would lose 4-1 to Arsenal and the club have been fighting in the lower tiers ever since.
It was Ben Watson's memorable header from a Shaun Maloney corner that broke the deadlock on the 91st minute, as it looked certain the game would go to extra time.
The Latics became and remain the first team in the history of English football to win the FA Cup and face relegation in the same season.
Sunderland 1-0 Leeds - 1973
The high-flying Leeds United were one of the best teams in Europe once upon a time and when they entered the 1973 FA Cup final, the Whites were the clear favourites over Sunderland.
However, despite being the current favourites and finishing third in the league, Leeds could not find away past the Division Two side at Wembley.
Ian Porterfield's first half goal became the difference that famous day, and as far as FA Cup final upsets go, this is one the greatest of all time.
Wrexham 2-1 Arsenal - 1992
Back in the 90s, Arsenal were winning something most years and both George Graham and Arsene Wenger had built trophy-winning sides in their own right.
And when Wrexham would meet Arsenal in the FA Cup of 1992, there was not even a sprinkle of hope from the North Wales side, given how the Gunners were the league champions just a year prior and how Wrexham were rock bottom Division Four.
In today's world, this would roughly translate to the side bottom of League Two and on course to be relegated, beating the Premier League champions.
Manchester United 0-1 Leeds United - 2010
Leeds are back again, but with an FA Cup upset of their own.
The Whites were relegated five years prior to this meeting and a clash between the two old rivals seemed as if it was not going to come for a long, long time.
However, a draw in the third round brought them together once more for the tie of the round, and with 42 places separating the two clubs, Leeds' victory became one they could boast about for years to come, despite only just achieving relegation back to the top flight recently.
This result was the first time United had ever lost at this stage in the FA Cup and the first time ever under Sir Alex Ferguson's leadership where a club from the lower tiers had beat them.
A true FA Cup upset and a memorable day for Leeds fans.
Hereford 2-1 Newcastle United - 1972
Whilst results like Wrexham's over Arsenal, The Crazy Gang's triumph and Wigan's win in 2013 tend to spring to mind when talking about the greatest FA Cup upsets of all time, this one is arguably the most shocking FA Cup upset ever.
Hereford hosted Newcastle United in 1972, as the Southern League Side had earned a draw at St James' Park, which in itself, was a historic FA Cup upset.
The side way down in the fifth tier were once again given little hope as they met the Magpies once again, but in the replay, Ricky George's winner sparked the most fabulous of scenes at Edgar Street and created one of them most magical FA Cup upsets of all time.
The FA Cup Giant-Killing award which formed in 2011 was originally called the Ronnie Radford award - the man who scored the opening goal for Hereford that day - this is how big of a deal this was.
Manchester United 0-0 Exeter - 2005
When Manchester United hosted Exeter City in the FA Cup back in 2005, barely a soul thought they'd leave with a replay, as the Red Devils were winning the Premier League every other year and currently held the FA Cup for the second time in six years.
Although it was a draw, and how Exeter would lose 2-0 in the replay, this was a team who were down in the non-league and travelled to arguably the toughest place in Europe and, the current champions of the competition.
Paul Scholes and Cristiano Ronaldo would end up coming on in the second half to snatch the win, but they and the likes of Wes Brown and Phil Neville couldn't get the job done and the non-league side would manage to upset the odds and earn a draw.
Shrewsbury Town 2-1 Everton - 2003
Shrewsbury Town were right near the bottom of the entire Football League back in 2003 and were staring in the face of relegation and becoming a semi professional team.
Two goals from Nigel Jemson would come against Everton in the FA Cup, however, in what became the upset of the tournament that year and arguably the biggest upset of the FA Cup in the noughties.
Chelsea 2-4 Bradford - 2015
Just two years after Wigan had stunned City in the FA Cup final, Bradford City would only go onto beat this feat, given how it was at Stamford Bridge, Chelsea were the Premier League leaders, and how Bradford were in League One.
Ever since Roman Abramovich took over Chelsea in 2003, very, very few teams have ever won at Stamford Bridge, never mind an outfit from two divisions below the Premier League.
Not just that, Bradford would score FOUR goals and earn them a place in the last 16. This was a truly magical FA Cup shock and arguably the biggest FA Cup upset of the last 20 years, given the stature of both sides and how it was on Chelsea's home turf.
Norwich City 0-1 Luton Town - 2013
Another upset which, in today's world, wouldn't be so dramatic, given how Norwich City and Luton Town are both in the Championship. However, back in 2013, the Canaries were up in the Premier League, whilst Luton were down in the Conference Premier and barely given a chance with the top flight club.
Scott Rendell would score in the 80th minute to cause bedlam in the away end and which would end up being the decisive goal that would mean Luton became the seventh team from non-league to reach the fifth round after World War II.
At the same time, it was also the first time a non-league side had beaten a top flight team in 24 years and the first time a non-league side had ever beaten a Premier League side; a record that still stands today.
A true FA Cup upset and one that may not been matched for some time.
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