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10 most memorable FA Cup upsets of recent times

Utathya Nag
Top 5 / Top 10
19.34K   //    Timeless

FA Cup has a history of major upsetsSomething seems very wrong with the FA Cup’s 5th round draw this year when compared to the Premier League table. The current leaders and second spot holders of England’s top-tier seems to have gone amiss from the world’s oldest footballing competition.The 4th round of the FA Cup saw a host of unprecedented results. Chelsea, currently the leaders of the Premier League, were unceremoniously shown the door by League One team Bradford City while the reigning champions Manchester City were upset by lower league side Middlesbrough. One might argue that a domestic cup without the two best teams in the country at the moment is somewhat uninspiring, especially in an age where the FA Cup seems to be losing its relevance in the face of more global events like the Champions League or the Europa League.What makes the FA Cup tick are exactly what the big top-league teams dread; the David vs Goliath battles with the same ‘biblical’ outcome. There are a few things in life more satisfying in life than an underdog coming out on a day and refusing to acknowledge the norm of natural hierarchy and sticking it to the favourites. For a neutral football fan, the FA Cup still serves the rare gourmet of watching the mighty fall.Throughout the history of the 143-year-old tournament, quite a few Davids have scalped their very own Goliaths. Here, we take a look at some of the most memorable upsets in recent memory of the FA Cup.

#1 Bournemouth 2 Manchester United 0 (1984)

Milton Graham scores against Manchester United

Third division team Bournemouth, managed by a young Harry Redknapp took on a Manchester United side who were challenging for the League title. Ron Atkinson’s side were also the reigning FA Cup champions at the time.

After a goalless first half, Bournemouth players seemed to grow in confidence and took the game to their more illustrated opponents. The Cherries seemed to have found a footing in the match and their confidence paid dividends when Milton Graham finished a corner past United’s Belgian goalkeeper Gary Richard Bailey.

United had barely come out of the shock, when minutes later when 25-year-old Ian Thompson picked up on a hesitation by United Legend Bryan Robson and put the unlikely winners 2-0 up.

In the frenzy, Manchester United supporters spilled onto the pitch in an effort to halt the game, but they only succeeded in delaying the fated result..

Skip to the end of the BBC newsreel for one of the vintage Harry Redknapp interview after the match.

#2 Liverpool 0 Wimbledon 1 (1988)

Vinnie Jones kisses the FA Cup after upsetting Liverpool at Wembley

There were a few teams bigger than Liverpool during the 1980s. Having secured the League, the Reds faced an unfancied Wimbledon side, who clawed themselves to the FA Cup finals riding on the bullying tactics of John Fashanu, Dennis Wise and current movie star Vinnie Jones.


The Wimbledon side, nicknamed the ‘crazy gang’ refused to lay down to Kenny Dalglish’s Liverpool side including the likes of Peter Beardsley, Steve Nicol, Nigel Spackman, John Barnes, Bruce Grobbelaar,  Alan Hansen, Ray Houghton and Steve McMahon to name but a few – all legends of Liverpool FC.

The perseverance sustained as Wimbledon took a shock lead owing to a Lawrie Sanchez header in the 37th minute.

The Liverpool side threw everything to come back into the game and seemed to have been finally awarded for their efforts with a penalty around the hour mark for a foul on John Aldridge by Clive Goodyear. The replay showed that Goodyear had won the ball cleanly. Up stepped Aldridge to take the spot kick, but Wimbledon’s captain goalkeeper Dave Beasant guessed correctly.

This was the first penalty save in the history of FA Cup finals at the Wembley. The London side hung on to win their first major trophy and cause one of the biggest upsets in the FA Cup’s illustrated history.

#3 Wrexham 2 Arsenal 1 (1992)

37-year-old Mickey Thomas drew Wrexham level

Arsenal arrived at Racecourse ground for the 3rd round FA Cup tie on 4th January 1992 as the reigning first division champions. The opponents, Wrexham were at the bottom of the 4th division back then.

Needless to say, the 13,343 attending the match did not expect much from the home team against the mighty Gunners. The match seemed to going by the script as Arsenal striker Alan Smith tapped in Paul Merson’s minus into the Wrexham net in the first half.

However, Wrexham’s 37-year-old captain Mickey Thomas decided to lead by example. Eight minutes from time, the Welshman drew the underdogs level after he beat Arsenal’s England international goalkeeper David Seaman with a 25-yard free kick.

Arsenal hardly got the time to recover from the shock when Steve Watkin put Wrexham 2-1 up and the home team held on to create a piece of history.

#4 Shrewsbury Town 2 Everton 1 (2003)

Everton’s Alan Stubbs tackles Shrewsbury’s Luke Rodgers

Former Everton player Kevin Ratcliffe managed his Shrewsbury Town team in the third round of the FA Cup in 2003. He entertained his former club at Gay Meadow in 2003. There was a difference of a whopping 80 places between the two clubs in the football league at the time and everyone was expecting an easy kick-around for the Merseysiders.

Shrewsbury’s striker Nigel Jemson curled home a 38th-minute free-kick to put the home crowd into a frenzy.

The lead lasted until almost the hour mark until substitute Nicholas Alexandersson came on for Everton at half time and made his impact by finishing neatly from a Scott Gemmill pass.

Everton, who by then were expected to bring home the win, created a lot of chances but finished to finish off the tie.

With a replay at Goodison Park looking likely and Shrewsbury already celebrating a hard earned draw, Jemson got on the end of Woan's last minute cross to head home the winner and send Shrewsbury to dreamland.

#5 Liverpool 1 Barnsley 2 (2008)

Petr Crouch was part of the Liverpool side which lost to Barnsley

Around 43,000 fans at the legendary Anfield Stadium could only rub their eyes in disbelief when a Barnsley team, 29 places behind them, stunned their more accomplished hosts. 

Liverpool boss Rafa Benitez decided to field a relatively weakened side, without Fernando Torres and left Steven Gerrard on the bench. However, the side was by no means a pushover, with starts for Jamie Carragher, Sami Hyypia, Riise, Benayoun, Lucas, Xabi Alonso, Dirk Kuyt and Petr Crouch.

Liverpool started like they meant business as Ryan Babel set up Dirk Kuyt for a 32nd minute opener. The Merseyside team seemed in control and would have easily run away with the game if not for one ex-Manchester United goalkeeper, Luke Steele.

Steele had signed for Barnsley on an emergency loan from West Brom, barely 48 hours before the match since Barnsley was badly hit by an injury crisis to the first team goalkeepers. Steele chose the day as his occasion and put in a display to behold to keep the minnows in the game.

The keeper’s inspired performance seeped into the outfield players as Barnsley found their equalizer in the 57th minute through Stephen Foster. A resolute defence and a genius Steele saw off the onslaught from the Premier League side. Even one Steven Gerrard failed to unlock Barnsley after coming on in the 75th minute.

Barnsley persevered and in injury-time, Brian Howard put in a low shot in Liverpool’s net to complete Rafa’s worst nightmare.

#6 Barnsley 1 Chelsea 0 (2008)

Kayode Odejayi puts a header past Chelsea keeper Carlo Cudicini

If someone tells you lightning doesn’t strike twice, ask them to google up 2008’s Barnsley team. After beating Liverpool in the 5th round, Barnsley met the reigning FA Cup champions, Chelsea.

Avram Grant decided to learn from Rafa Benitez’s mistake and decided to put in most of his £200 million worth of firepower to counter a Barnsley team which cost £350,000.

Chelsea unleashed high profile players such as Ricardo Carvalho, John Terry, Michael Ballack, Florent Malouda, Nicholas Anelka, Joe Cole and Michael Essien, but they couldn't find a way past Barnsley's stubborn defence, which seemed to pick up from where they left at Liverpool.

However, the match would be memorable because of a historic bit of commentator’s curse by John Motson (yes the same guy from Fifa video games).

Motson, around the 65th minute said, “Odejayi wouldn't mind a diagonal cross here”. Barnsley winger Martin Devaney responded with a cracking cross and Barnsley’s Nigerian striker Kayode Odejayi rose to put a header past Chelsea keeper Carlo Cudicini. It was Odejayi’s first goal in 29 matches. Barnsley held on to reach the semi-finals for the first time since 1912.

Incidentally, the Titanic sank in 1912.

#7 Manchester United 0 Leeds United 1 (2010)

Jermaine Beckford scores past Thomas Kuszczak

The rivalry between Manchester United and Leeds United has often been termed by the nickname ‘Roses rivalry’. The enmity between the two northern clubs over the years has been more synonymous to the thorn than the flower. 

In what even Sir Alex Ferguson describes as a ‘feisty occasion’, the two teams locked horns in the FA Cup third round tie in 2010.

The match held particular importance to Leeds fans. After the Yorkshire team was relegated from the top division of English football in 2004, the two sides had rarely met. While the Manchester United fans had moved on to call Liverpool or Manchester City their biggest rivals, Leeds fans still considered United their sworn footballing rivals.

The two sides met at Old Trafford with 42 league places separating them. However, Leeds were in good form having gone unbeaten in 15 under manager Simon Grayson.

Ferguson fielded a weakened team, but with Wayne Rooney and Dimitar Berbatov leading the line, the Reds certainly didn’t lack firepower.

Leeds started off by frustrating United and in the 19th minute, Jermaine Beckford escaped Wes Brown to put Leeds in the lead. A frantic United tried to come back bringing in Ryan Giggs, Antonio Valencia and Michael Owen off the bench but a resolute Leeds combined with some awful finishing handed Sir Alex Ferguson his first defeat to lower League oppositions in the 3rd round of the FA Cup, in his 23 years of managing Manchester United.

#8 Manchester City 0 Wigan Athletic 1 (2013)

A dejected Manchester City side after losing to Wiga

Even though both the teams involved in 2013 FA Cup finals were part of the Premier League, the consequences involving the match makes it one of the biggest upsets in FA Cup in the modern era.

Manchester City were last season’s Premier League champions who had been outdone by Sir Alex Ferguson’s Manchester United to the title that season. Roberto Mancini’s side in an attempt to salvage some pride decided to go full strength when they took on a struggling Wigan side in the final. Wigan were at the time fighting a losing relegation battle while City were trying to lift the FA Cup for the second time in three years.

City lined up with the likes of Sergio Aguero, Yaya Toure, and David Silva in their team, but the Latics played with real adventure. Ben Watson headed in the only goal of the game in the final minutes.

The match proved Roberto Mancini’s last match as City manager. Wigan were relegated from the top-flight just three days after their famous win.

#9 Chelsea 2 Bradford City 4 (2015)

Filipe Morais celebrates the equalizer against Chelsea

Chelsea manager Jose Mourinho has time and again reiterated that the FA Cup holds little interest to the ‘Special One’. However, even the Portuguese seemed irritated after Chelsea lost to League One side Bradford City 2-4.

Chelsea, going into the match as the leaders of the Premier League, seemed to be in a hurry to wrap things up in front of their home crowd. 

Gary Cahill put the hosts ahead after 21 minutes and Brazilian midfielder Ramires put the Blues 2-0 up as the Premier League side seemed to be cruising to victory. Jon Stead’s goal just before the half-time gave the Bantams a glimmer of hope.

However, that seemed like all the League One side was looking for as Bradford rallied in the 2nd half with goals from Filipe Morais, Andy Halliday and Mark Yeates.

Stamford Bridge was shocked and Jose Mourinho termed the defeat as ‘disgraceful.

#10 Manchester City 0 Middlesbrough 2 (2015)

Patrick Bamford after putting Middlesbrough in the lead

On the same day Bradford upset Chelsea, Middlesbrough travelled to reigning champions Manchester City, positioned second after an impressive Chelsea in the League.

Boro striker Patrick Bamford, a loanee from Chelsea decided to deny City the pleasure of seeing their closest competitors bow out of the FA Cup. 
A defensive lapse saw Bamford take advantage and put the Championship side ahead. Boro keeper Tomas Mejias producing several smart saves to keep his side in the game.

Substitute Frank Lampard came close to salvaging some pride for the reigning League champions and earn a replay. But his attempt came off the post. Minutes later, Bamford turned provider as Kike caught hold of the youngster’s pass and finished the game off.

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