Ajax produced a stunning performance and shook the footballing world last night as they dumped holders Real Madrid out of the Champions League in the round of 16.

Trailing 2-1 from the first leg, the Amsterdam outfit travelled to the Santiago Bernabeu facing a decidedly uphill battle for qualification. However, Erik ten Hag's men stunned their hosts 4-1 thanks to goals from Hakim Ziyech, David Neres, Dušan Tadić and Lasse Schöne. 


After Real secured an away leg victory at Johan Cruijff ArenA, few would have given Ajax a hope of progressing. An even smaller number would have predicted that the visitors would rout Los Blancos and secure what was ultimately a relatively straightforward win.

The game was undeniably one of the biggest upsets in the history of the Champions League. Here's a look at some other major surprises that the competition has thrown up in the past.

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Dynamo Kiev 2-0 Real Madrid (17 March 1999)


Given the events of last night, it is only fitting to begin with another astonishing Real exit. In this encounter, the 13-time winners were humbled by Ukrainian outfit Dynamo Kiev as they fell at the quarter-final stage.

Following a 1-1 draw in the first leg, the holders arrived at Olympiyskiy Stadium knowing they had to score. They didn't. A second-half brace for Andriy Shevchenko sealed victory for the home side as they continued their remarkable march into the latter stages of the tournament. 

Unfortunately for Shevchenko and co. they were eliminated by Bayern Munich in the next round.

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BATE Borisov 3-1 Bayern Munich (2 October 2012)


They may have brought an abrupt end to Dynamo's fairytale in 1999, but Bayern are not exempt from upsets themselves. One of the more unexpected results in their illustrious European history came in Belarus against BATE Borisov.

The Bavarians were humbled 3-1 by the minnows in the group stages of the 2012-13 Champions League. Jupp Heynckes had fielded a strong side for the game, with Manuel Neuer, Toni Kroos and Franck Ribéry starting in a star-studded lineup, yet were unable to avoid embarrassment.

Bayern's impressive squad for the match, as well as the fact that they went on to lift the trophy later that season, stands testament to the magnitude of this shock.

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Barcelona 1-2 Rubin Kazan (20 October 2009)


Losing to Rubin Kazan in any match is unacceptable for footballing royalty like Barcelona. That this defeat came at the Camp Nou rubs salt into the wounds.

A memorable result was on the cards from early on as the Russians took a second-minute lead in Catalonia thanks to a long-range piledriver from Alexander Ryazantsev. Despite being pegged back by Zlatan Ibrahimovic just after the break, the underdogs claimed a hugely unlikely three points late on. 

Pep Guardiola's Barça were one of the greatest sides ever assembled, yet Messi, Xavi and Iniesta all went missing on an astonishing Tuesday night.

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Celtic 2-1 Barcelona (8 November 2012)


Guardiola is not the only Barcelona manager to have endured a surprise defeat. The season after his departure, Tito Vilanova was the man in the dugout for a ludicrous loss at Celtic Park.

Describing this match as one-sided does not do justice to the on-field events. The hosts had five shots to Barcelona's 23 and were afforded just 11% of possession. The Catalans also completed almost 800 more passes during the contest. Of course, the only statistic that mattered was that the Scots netted twice and Barça only once.

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Helsingborg 1-0 Inter (9 August 2000)


Italian giants Inter failed to reach the group stages of the 2000-01 Champions League as they were edged out by Swedish club Helsingborg in their qualifier. 

Michael Hansson popped up with a late score in the first leg, giving the Swedes a lead to protect and an outside chance of progression in the return fixture. They achieved this improbable feat the following week, frustrating the three-time European champions during a 0-0 stalemate at the San Siro.

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Barcelona 2-3 CSKA Moscow (4 November 1992)


In this encounter, it was once again a Russian club who handed Barcelona an unexpected defeat.

This knockout tie was level when the Muscovites ventured to the Camp Nou for the second leg. Home advantage made Guardiola and his teammates strong favourites to reach the next round and this looked even more probable when they took a two-goal lead.

Unfortunately for the Spaniards, a 17 minute blitz saw CSKA take a stranglehold and they maintained this grip on the game until the final whistle. 3-2 it finished on the night, Johan Cruyff's side crashing out 4-3 on aggregate.

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APOEL Nicosia 1-0 Lyon (8 March 2012)


APOEL Nicosia qualifying from their group in 2012 was an incredible achievement in itself. The Cypriots then outdid themselves, toppling Lyon in the next round to set up a quarter-final clash with Real Madrid where they were ultimately eliminated.

This Lyon outfit were a powerhouse of French football at the time, having won Ligue 1 on seven separate occasions in the preceding decade. They took a one goal lead to Cyprus, yet found themselves level on aggregate going into extra-time after an early strike from Apoel's Gustavo Manduca.

Neither side found a winner thereafter and thus penalties were required. In storybook fashion, Apoel emerged victorious from the shootout, with Hugo Lloris unable to prevent a momentous result.