Sheriff Tiraspol 2-1 Real Madrid – 2021-22
Statistically the most shocking result in Champions League history. Moldovan club Sheriff Tiraspol had a 1.4 percent chance of beating Real Madrid at the Bernabeu when the two sides met in the group stage.
A first-half goal from Jasurbek Yakhshiboev put the debutants ahead before Sebastien Thill’s audacious 89th-minute volley completed one of the most extraordinary results the competition has ever produced. Real Madrid, 13-time European champions, were beaten at home by a club most of Europe had never heard of.
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Liverpool 3-3 AC Milan – Istanbul, 2005
AC Milan were 3-0 up at half-time in the Champions League final and in cruise control, looking set to claim their seventh European crown. What followed in the second half has never been matched.
Steven Gerrard, Vladimir Smicer and Xabi Alonso scored three goals in six second-half minutes to level the match. Jerzy Dudek’s save from Shevchenko in extra time and a penalty shootout victory completed the most dramatic comeback in the history of the final. The Miracle of Istanbul.
Ajax 4-1 Real Madrid – 2018-19
Ajax produced a stunning performance to dump holders Real Madrid out of the Champions League in the round of 16, with goals from Hakim Ziyech, David Neres, Dusan Tadic and Lasse Schone completing a remarkable 4-1 win at the Bernabeu.
Real had won the previous three Champions League titles. Ajax were a side of wonderkids – De Ligt, De Jong, Ziyech – who had no right to be that dominant on that stage.
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Deportivo La Coruna 4-0 AC Milan – 2003-04
Milan won the first leg 4-1 and the tie appeared over. Deportivo had other ideas.
Walter Pandiani, Juan Carlos Valeron, Albert Luque and Fran scored as Deportivo completed one of the greatest quarter-final comebacks in the competition’s history, winning 4-0 to go through on away goals. A result that remains one of the most remarkable in European football.
Inter Milan 3-1 Barcelona – 2009-10
Jose Mourinho masterminded one of the greatest tactical displays in Champions League history as Inter Milan defended resolutely, neutralised Lionel Messi and struck decisively on the counter-attack to eliminate Guardiola’s Barcelona in the semi-finals.
In the first leg at the San Siro, goals from Maicon, Wesley Sneijder and Diego Milito gave Inter a commanding 3-1 advantage over the reigning champions.
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The second leg at the Camp Nou was even more remarkable. Thiago Motta was controversially sent off after 28 minutes following a clash with Sergio Busquets, leaving Inter with 10 men for over an hour against the most dominant side in the world.
Mourinho sprinted onto the pitch at the final whistle at the Camp Nou – one of the most iconic images the competition has ever produced. Inter went on to beat Bayern Munich 2-0 in the final in Madrid, completing the treble under Mourinho.
Photo: Claudio Villa/Getty Images
