Legends: The 25 greatest upsets of all time


The giant killing – one of football’s greatest legends. Over the past 50 years, there have been some sensational surprise stories.
Sometimes it might have been luck, other times it was fate and destiny and on some occasions, it was when the most unlikely of teams possible, outperformed their classy opponents and won the biggest prizes in the game.
The World Cup, European Championships, the FA Cup, Premier League and African Cup of Nations all feature in this list of upsets.
Total Football’s Simon Wright has come up with his list of 25 greatest upsets of all-time.
There was a big shortlist to compile from the last 50 years and some haven’t made the top 25.
Those that came close to breaking through include:
• Bournemouth’s 2-0 victory over Manchester United in the 1984 FA Cup third round.
• Mexico’s recent Olympics success over Brazil in the final.
• The Faroe Islands shocking Austria in a 1990 friendly.
• Fulham’s Europa League fightback against the mighty Juventus in 2010.
• South Korea dumping Italy out of the 2002 World Cup.
So, who made the list in the 25 greatest upsets of all-time?
25. Costa Rica 1-0 Scotland, World Cup Group C, 11 June 1990
Scotland’s record in major tournament football is pretty disastrous but everyone expected them to beat novices in the World Cup, Costa Rica.
In typical Scottish fashion, they blew it again and became victim to a surprising upset in their Italia 90 opener.
The Central Americans were managed by Bora Milutonivic, who had guided Mexico to the quarter-finals in 1986.
They defended brilliantly and shortly after the interval, took the lead through striker Juan Arnaldo Cayasso.
The Scots failed to materialise a severe rampage afterwards and were humiliated on the world stage again. They made their traditional exit at the group stage, whilst the Costa Ricans made the knockout rounds, before losing 4-1 to Czechoslovakia.
24. Barcelona 0-0 Steaua Bucharest, European Cup final, 7 May 1986 (Steaua Bucharest WON 2-0 on penalties)
It is very unlikely that you will see a Romanian side, win the biggest prize in European club football again.
Steaua Bucharest defeated the odds and a much stronger Barcelona side to win the European Cup in 1986, a Barca side managed by Terry Venables.
The game itself was dull, with the favourites doing the attacking and the underdogs playing for penalties from the start.
Their gameplan worked, as Helmuth Duckadam saved all four penalties from the Catalans, becoming the ‘Hero of Seville.’
Steaua won 2-0 on penalties to bring the big prize, back to Eastern Europe. It wasn’t pretty but effective and it is always nice to see the little guys win.
23. Liverpool 2-2 Northampton Town, League Cup third round, 22 September 2010 (Northampton Town WON 4-2 on penalties)
I’m a Liverpool fan and at the time, studying at the University of Northampton. This was a humiliating experience, although great for the town I was living in during my degree.
One of Liverpool’s darkest ever results, as they dumped out by a team that were 69 places below them on the football ladder.
Everything looked like it was going to the formbook, when Milan Jovanovic gave the Reds a ninth minute lead, only for Billy McKay, to smash in a second half equaliser and take the game into extra-time.
Michael Jacobs drove the League Two strugglers ahead in extra-time and a win in regulation time looked likely, until David N’Gog spared blushes briefly, with a 116th minute leveller.
As the rain crashed down on Merseyside, the Reds usual penalty accuracy went missing. N’Gog and Nathan Eccleston both missed, allowing Abdul Osman to slot home and provide one of Northampton’s greatest triumphs.
Roy Hodgson’s reign at Anfield was forgettable and this was ultimately, the absolute low point.
22. Manchester United 0-3 York City, League Cup second round, 1st leg, 20 September 1995
Slightly weakened perhaps but this night did see a Manchester United side that fielded Ryan Giggs, David Beckham, Gary Pallister and Lee Sharpe.
Third division York City recorded their most famous victory, with two goals from Paul Barnes and a third late on from Tony Barras.
Alex Ferguson was furious and fielded the big guns at Bootham Crescent for the second leg but could only win 3-1 and so, got dumped out on aggregate.
Despite this, they still won the league and FA Cup double that season.
21. Chelsea 0-3 Sunderland, FA Premier League, 14 November 2010
Chelsea had started their Premier League defence in formidable form and only lost two games so far, away at Manchester City and Liverpool.
This shock home defeat to a Sunderland side battered 5-1 at local rivals Newcastle only a fortnight earlier, stunned the Premier League and started a capitulation for the champions.
Defender Nedum Onuoha scored a brilliant solo goal on the stroke of half-time, before some lovely build-up involving Danny Welbeck and Jordan Henderson, allowed Asamoah Gyan to slot home a second.
Ashley Cole’s dreadful defensive backpass, allowed Welbeck in for a third in the last five minutes, completing the best day of Steve Bruce’s inconsistent time as manager of the Black Cats.
20. Northern Ireland 1-0 England, World Cup qualification, 7 September 2005
Sven-Goran Eriksson didn’t endear himself to many as England manager but his qualifying record for major tournaments was pretty impressive.
However, there is one evening English football will want to forget, as they were embarrassed by a Northern Ireland side that might have been ranked over 60 places lower but were the better side.
David Healy scored the only goal, collecting Steven Davis’s long ball to thrash the winner past David James on 73 minutes. This was their first win against England in 33 years.
The Three Lions were abject throughout and never looked scoring, despite starting with Wayne Rooney, Beckham, Michael Owen and Frank Lampard.
It was a painful defeat for England but a night that Northern Irish fans will never forget.
19. Spain 0-2 USA, Confederations Cup semi-final, 25 June 2009
Spain arrived at the Confederations Cup, unbeaten since 2006 and on a world record run for successive victories in international football.
However, they fell foul to the power of the USA, who reached the final with a classy performance.
Jozy Altidore broke the deadlock on 27 minutes and after Tim Howard had denied David Villa and Fernando Torres, Clint Dempsey finished the Spanish off, when he drilled in a Landon Donovan pass from close range.
Spain’s record ended at 15 consecutive wins and 35 matches unbeaten but it was only a minor hiccup in their recent tournament football domination.
18. Germany 1-2 Bulgaria, World Cup quarter-final, 10 July 1994
Before the World Cup in 1994, Bulgaria had never won a match in the finals.
Having already knocked out Mexico and beaten Argentina in the group stages, they met world champions Germany in the last eight.
When Iordan Letchkov gave away a penalty, dispatched by Lothar Matthaus, the game was going by the formbook.
The Eastern Europeans showed great character and were level through their talismanic figure, Hristo Stoichkov. Then against the odds, Letchov sneaked infront of his marker to power a header past Bodo Illgner.
The holders were out in a World Cup that provided plenty of surprising results in humid conditions.
17. Artmedia Bratislava 5-0 Celtic, UEFA Champions League 2nd qualifying round, 1st leg, 27 July 2005
Slovakian champions Artmedia Bratislava dished out a real surprise and with it, Celtic’s biggest and most humble defeat in Europe.
The Scottish defence fell apart in Bratislava, as Juraj Halenar netted a very unlikely hat-trick.
Blazej Vascak and Martin Mikulic added to the misery for Gordon Strachan, in his first game in the job.
Celtic did win the second leg 4-0 but they were eliminated and to show it wasn’t a fluke, Artmedia went onto beat FC Porto, in Portugal in the group stages.
16. Barnsley 1-0 Chelsea, FA Cup sixth round, 8 March 2008
With Liverpool, Arsenal and Manchester United all out of the FA Cup before this tie, cup holders Chelsea were expected to cruise to the Wembley final.
Nobody told Barnsley, as the Championship side made the semi-finals for the first time since 1912, on an unforgettable night at Oakwell.
Kayode Odejayi’s header on 66 minutes proved to be the difference, his first goal since September.
The Tykes held on, to give Simon Davey his greatest moment in club management and pile the pressure on Avram Grant, as the Blues won nothing by the end of the season.
15. AS Monaco 3-1 Real Madrid, UEFA Champions League quarter-final, 2nd leg, 6 April 2004
Real Madrid’s great ‘Galacticos’ missed a golden opportunity to win the trophy, in this most open of Champions League seasons in recent times.
4-2 ahead from the first leg in Spain, Raul added to the total, ten minutes before half-time.
Ludovic Giuly’s sweet equaliser, offered hope to Monaco but they came out more determined and motivated in the second half.
On loan from Madrid, Fernando Morientes gave his parent club more to worry about and Giuly completed the remarkable turnaround and take a small club into the semi-finals.
They reached the final before losing to Jose Mourinho’s FC Porto. For Madrid, their galaxy of stars, including Figo, Zidane, Ronaldo, Beckham and Raul had failed to deliver on so much talent.
14. Wolves 1-0 Manchester United, FA Premier League, 17 January 2004
As commentator Alan Parry said at the time: “Do not adjust your TV set, Wolves have just taken the lead against Manchester United.”
It was bottom versus top at Molineux and few gave Dave Jones’s basement boys a chance, against the Red Devils, who had only lost three times in the season so far.
Rio Ferdinand limped off injured and into his eight month ban for missing a drugs test and despite controlling possession, Sir Alex Ferguson’s team, were caught cold by Kenny Miller.
The Scot glided past Wes Brown and slotted the ball coolly past Tim Howard to record one of the biggest upsets in FA Premier League history.
13. Barcelona 1-2 Rubin Kazan, UEFA Champions League Group F, 20 October 2009
Champions of Europe and with Xavi, Lionel Messi and Andres Iniesta amongst their ranks, Barcelona were on the receiving end of one of the greatest upsets in European club football.
Aleksandr Ryazantsev gave the unknown Russians, Rubin Kazan a shock advantage after only two minutes, a lead they held until early in the second half, thanks to a Zlatan Ibrahimovic leveller.
Just when those watching in the Nou Camp thought business would return to normal, a careless pass from Xavi, enabled Gokdeniz Karadeniz in, to stun the footballing world.
Rubin Kazan might have not escaped the group but they had their moment in the spotlight, highlighting the recent surge in fortunes that has made Russian football, a very enticing proposition.
12. Denmark 2-0 Germany, Euro 92 final, 26 June 1992
Denmark weren’t even meant to play in Euro 92. They were only called in as last minute replacements for Yugoslavia, banned after civil war had hit the country.
They escaped a group that contained France and England, before shocking holders Holland in the semi-finals.
The fairytale was complete in the final, when not many gave them a hope against the reigning world champions.
Goals in each half from ex-Arsenal no-hoper John Jensen and Kim Vilfort completed the remarkable story, giving Denmark their finest hour and one of the greatest fairytales to come true.
11. Switzerland 1-2 Luxembourg, World Cup European qualifying Group 2, 10 September 2008
Luxembourg is one of the tiniest European nations and traditionally, the whipping boys in any qualifying group they are drawn in.
Even they had their moment in the spotlight, when they stunned Switzerland in Zurich, during qualifying for World Cup 2010.
There might have been 109 places between the two sides but since when was a match decided through a ranking system?
Alphonse Leweck came off the bench to grab the winner with four minutes to go, as the visitors claimed a historic win.
Switzerland did recover to top this group and even beat Spain during the finals in South Africa.
10. North Korea 1-0 Italy, World Cup group phase, 19 July 1966
Middlesbrough’s Ayresome Park played host to a major upset in the 1966 World Cup, as the mighty Italy were caught out by debutants in the finals, North Korea.
Doo-Ik Pak scored the solitary goal after 41 minutes. It is a result that is still fondly remembered by North Koreans and one that the Italians still painfully get reminded of.
9. Hereford United 2-1 Newcastle United, FA Cup third round replay, 5 February 1972
Hereford United created FA Cup folklore in 1972, when the Southern League side eliminated first division Newcastle United, amidst scenes of joy on a muddy Edgar Street field.
The first instalment had finished in a 2-2 draw and the replay, had been postponed three times previously due to bad weather.
The game was closely contested, until a Malcolm Macdonald header with eight minutes left, looked as though it was going to be enough.
Three minutes later, part-time carpenter Ronnie Radford struck one of the most iconic goals in the history of the cup, forcing a crowd invasion and the game into extra-time.
Radford had a part in the winning goal too, setting up Ricky George, who scored in the 103rd minute.
The Magpies were stunned and Hereford held on, for their most famous result in their history.
8. France 0-1 Senegal, World Cup Group A, 31st May 2002
African newcomers to the World Cup, Senegal, shocked world and European champions France, to win the first game of the 2002 World Cup in Seoul.
A defensive mix-up between Emmanuel Petit and Fabien Barthez, allowed Papa Boupa Diop to score the only goal on the half hour.
This was one of the biggest upsets in World Cup history, as the decline of this great dynasty of French players had started in the most unceremonious of ways.
7. Sutton United 2-1 Coventry City, FA Cup third round, 7 January 1989
Gander Green Lane played host to the last time a non-league side eliminated a club from the top flight of the FA Cup.
Coventry City had won the FA Cup in glorious fashion in 1987 but only two years later, they were victim to a staggering upset against part-timers Sutton United.
Left back and captain Tony Rains headed the GM Vauxhall conference team infront, three minutes before half-time.
Six minutes into the second half, Welsh international David Phillips put Coventry level but this only spared the blushes for a short time.
Seven minutes later, another Sutton corner saw Matthew Hanlan drill in from close range to restore Sutton’s lead and create a historic story.
6. Celtic 1-3 Inverness Caledonian Thistle, Scottish Cup third round, 8 February 2000
Having slipped ten points behind Rangers in the SPL, Celtic needed a good Scottish Cup run. Instead they ended up with the worst result of their history.
First division part-timers, Inverness Caledonian Thistle rocked Parkhead, with an awesome display that made Celtic look like semi-pros, not professionals.
The heroes for the visitors were Barry Wilson and Paul Sheerin from the penalty spot and along with an own goal from Lubomir Moravcik, sent the away fans into bedlam.
Unsurprisingly, manager John Barnes was lynched by home supporters and he resigned as manager shortly afterwards.
5. Ivory Coast 0-0 Zambia, African Cup of Nations final, 12 February 2012 (Zambia WON 8-7 on penalties)
In April 1993, a very talented Zambian football team was wiped out in a plane crash. 30 members, including 18 of the playing squad, were killed off the coast of Gabon, as they were travelling to Dakar to play Senegal in a World Cup qualifier.
19 years later, a new generation of Zambia football players turned up again in Gabon, this time for the African Cup of Nations and no-one in football gave them a chance.
This is African football though and they stunned the likes of Senegal and Ghana to reach the final, against heavyweights of the continent, the Ivory Coast.
They kept the Ivoirians contained, although Didier Drogba blazed a penalty over the crossbar in regulation time.
After 14 successful spot kicks in the shootout, Kolo Toure of Manchester City had his penalty saved and Arsenal’s Gervinho missed, allowing Stopila Sunzu of TP Mazembe to become a national treasure.
This was a victory for Zambia, a victory full of pride and fate and a victory for the lost generation of 1993.
4. Wrexham 2-1 Arsenal, FA Cup third round, 4 January 1992
League holders Arsenal were having an indifferent season but no problems were predicted against lowly Wrexham at the Racecourse Ground.
The Welsh club fell behind a minute before half-time, when Alan Smith poked home a Paul Merson cross.
Former Welsh international Mickey Thomas had other ideas though. The 37-year-old fired an unstoppable free-kick past David Seaman with eight minutes to go.
Then, two minutes later, Steve Watkin stabbed home the most unlikely of winners, as the Gunners and George Graham were left with red faces. Sometimes, David can beat Goliath.
3. Cameroon 1-0 Argentina, World Cup Group B, 8 June 1990
Italia 90 was a tournament where defensives ruled and negative football was the order of the competition.
However, there was an amazing result in the very first match, when holders Argentina fell to a surprising defeat to ‘The Indomitable Lions’ of Cameroon.
Cameroon’s physical approach did seem to backfire, when Andrea Kana Biyik saw red early in the second half, for a bad challenge on Claudio Cannigia.
Moments later, Francois Oman Biyik escaped his marker from a free-kick and guided a header past Nery Pumpido.
With Diego Maradona well marked out of the game, the Africans held on for an amazing result, despite Benjamin Massing’s brutal tackle on Cannigia which earnt him a blatant red card in the closing stages.
On this day, Argentina found out that Italia 90 wasn’t going to be all about style and substance.
2. Wimbledon 1-0 Liverpool, FA Cup final, 14 May 1988
Chasing another league and cup double, Liverpool ruled English football in the 1980s and everyone expected them to turn up at Wembley and stroll past Wimbledon in the 1988 FA Cup final.
The Crazy Gang had bags of spirit and this overcame the individual talent on display, from the likes of Barnes, Beardsley and Aldridge.
The only goal arrived on the half hour, a typical Wimbledon goal. Dennis Wise’s free-kick was headed home by striker Lawrie Sanchez.
Dave Beasant went onto make FA Cup final history, becoming the first goalkeeper to save a penalty in the final, from a despairing Aldridge.
This was the biggest shock of them all in the world’s greatest cup competition, the FA Cup.
1. Portugal 0-1 Greece, Euro 2004 final, 4 July 2004
The number one upset of all-time is Greece stunning the world, to win Euro 2004 against all expectations.
They may not have been very attractive to watch, nor were they the best side but what they were, was a team.
It was a perfect example of individuals not winning football matches but teams triumphing instead.
They arrived at the finals as massive underdogs but played party pooper in the group stages, beating the hosts on day one and qualifying for the quarter-finals, at the expense of Spain.
The Greeks then dethroned reigning champions France in the last eight, before a Traianos Dellas header sunk the Czech Republic in the semis, via the controversial ‘silver goal’ method.
It was back to Lisbon for the final and a rematch with Portugal. Despite their opening success over the Portuguese, still nobody believed Otto Rehhagel’s team could pull it off again.
They did though, with Angelos Charisteas heading home an Angelis Basinas corner, ten minutes into the second half.
Hard pressing and a solid defensive display afterwards, was enough to break Portuguese hearts again and surprise the world.
This proves that in the game of football, anything is possible.
You will have your own favourites but one thing everyone within football should be aware of; never underestimate the power of the underdog.
NEXT TIME ON THE GREATEST: Masterminding success, the ten greatest managers of all-time.
By Simon Wright – Follow me on Twitter @Siwri88

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