The 20 Greatest Defeats Of All Time (No. 20-16)

Following on from my article about reasons of defeat, I have compiled a list of defeats, which have caused a great impact in the course of footballing history. Here is the first five…of which most have been chosen of the circumstances and the drama involved.

Inter Milan 0 – 5 AC Milan 2005 Champions League Quarter Final
One of the most infamous Milan derbies in recent history, with a 2-0 lead from the first leg, AC were set to win, with a 1-0 lead from Shevchenko when the unruly Inter Ultras struck in protest to a goal from Argentine Cambiasso ruled out by referee Markus Merk. The objection consisted of bottles and debris being thrown onto the pitch and soon escalated to lit flares, one of which hit Milan keeper Dida on the shoulder, suffering first-degree burns. Therefore, the game was abandoned and Milan were awarded a 3-0 win, and the Nerazzurri fined €200,000, a UEFA record.


Bayern Munich v Manchester United 1999 Champions League Final
Three minutes of injury time had changed the outcome of this game. Man United had played poorly in Barcelona and it seemed to be Bayern’s trophy. The Bavarian club’s ribbons had been attached onto the cup, and it was only till after Munich substituted Basler and Matthaus that United came back into the game. A scuffed Giggs shot reached Sheringham, who scored from six yards. Then came another Beckham corner as ITV commentator asked: ‘is this their moment?’ Sheringham headed the ball down and Solskjaer instinctively swung his boot at the ball and lashed it into the roof of the net with virtually the final kick of the game. Having played an effective counter-attacking game-plan and hit the woodwork a number of times, against all the odds, the Mancunians completed the infamous treble and rival fans would never hear the end of it.

AC Milan 3-3 Liverpool 2005 Champions League Final
An impossible defeat. A Milan side, who scored inside a minute, and tore Liverpool to shreds through the clever running of Kaka, the smart passing of Pirlo and the killer instinct of Crespo and Shevchenko. It should have been four, if not for a poor decision by the linesman to deny Milan a fourth before the half time whistle. Then inside a six minute period, doubts crept into Milanese minds, when Gerard scored with a looping header. Reminders of previous matches against Deportivo La Coruna and close scares against Lyon and PSV Eindhoven cropped up. Even after the score was level, now cult hero Jerzy Dudek made to awesome saves from Shevchenko in the dying moments of extra-time at point-blank range. The penalty shoot-out brought out a Grobbelaar-esque instinct in Dudek who won the cup for the Merseyside club. Milan took revenge two years later.

USA 1-0 England 1950 World Cup First Round
Dubbed ‘Miracle on Grass’, it also has a film made after it released in 2005. This defeat finally took away the English belief of superiority in the game of football, and it displayed an urgent need to change the outlook upon the English game. New styles were being developed; most were tactically and aesthetically superior. Having refused to play against countries against whom they had fought in the war previously, and arguments on bonuses amongst other things, they finally arrived in Brazil, ready to prove their dominance. Or so they hope. Gaetjens scored against in defiance to the English dominance. It was beautifully summed by victorious American footballer Harry Keough in the aftermath through, ‘Boy, I feel sorry for these bastards. How are they ever going to live down the fact we beat them?’


Liverpool 0-2 Arsenal 1989 Division One
It was the final game of the season. Arsenal was trailing by three points. Liverpool was ahead on goal difference. The situation to George Graham’s Gunners was clear. They had to win by two clear goals. For Liverpool defeat was unthinkable and not a possibility against an Arsenal side with a defeat and a draw in their previous two home games. Enter Michael Thomas. Arsenal was leading by a goal through Alan Smith. Appeals of offside were waved away, and the final seconds are remembered by Brian Moore’s commentary: ‘Thomas, charging through the midfield... it's up for grabs now... Thomas, right at the end!’ Liverpool had lost in unbelievable circumstances.