The Greatest Quarter-Final Upsets in Champions League history

Published 04/04/2017, 3:34 PM EDT

The quarter-finals of the 2016-17 edition of the UEFA Champions League are just round the corner with adrenaline-pumping clashes like Bayern Munich vs Real Madrid and Juventus vs Barcelona lined up for the footballing fraternity to watch. However, there’s one fixture – Atletico Madrid vs Leicester City – which has the potential to send major shockwaves across the sporting world. Just imagine the scenes if Spanish heavyweights Atletico Madrid, who have reached the finals of the Champions League in the last three years, are defeated by Champions League debutants, Leicester City. Of course, the odds of this happening are low, but, what makes this match more interesting is the fact that the English champions defeated Sevilla(who have won the UEFA Europa League for the last three seasons) in the Round of 16, topped their group in the first round of the Champions League and are on a winning run in the Premier League since the acrimonious sacking of Claudio Ranieri. Atletico, on the other hand, are 10-points behind league-leaders Real Madrid in the La Liga and haven’t been at the goal-scoring best most of the season. Moreover, the Champions League has seen some outrageous upsets in the quarter-final stage over the years. Here’s a look at the best five among them:


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5. Villareal vs Internazionale (2005-06):


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Villareal players celebrate their victory over Inter

Unlike today, Internazionale were one of the major clubs in Europe about a decade ago, having the likes of Marco Materazzi, Juan Sebastian Veron, Javier Zanetti, Esteban Cambiasso and Luis Figo in their lineup. Coming in to this game, Manuel Pellegrini’s Villareal were the underdogs. Diego Forlan gave the Spanish side an early at the San Siro in the first leg, which was, however, overturned by Adriano and Obafemi Martins as Inter won the game. In the return leg though, Villareal held on to the lead given to them by Rodolfo Arruabarrena, as they knocked out the Italian giants on away goals.

Internazionale 2-1 Villareal (First Leg)

Villareal 1-0 Internazionale (Second Leg)

4. AS Monaco vs Manchester United (1997-98):

Monaco defeating Manchester United was one of biggest events in the 1997-08 Champions League

A Manchester United squad which won a historic treble in the 1998-99 season was defeated by minnows Monaco in the quarter-finals of previous year’s Champions League. After a stalemate in the first leg in France, would-be Arsenal legend David Trezeguet fired an emphatic strike as early as the 5th minute to give Monaco the lead at Old Trafford. Though United managed to pull one back through Ole Gunnar Solskjær in the 53rd minute, it wasn’t enough as Monaco went through to the semis on away goal, thus putting an end to the Red Devils’s attempt of claiming the coveted trophy for the second time in 30 years.

AS Monaco 0-0 Manchester United (First Leg)

Manchester United 1-1 AS Monaco (Second Leg)

 3. Dynamo Kyiv vs Real Madrid (1998-99):

Dynamo Kyiv pulled of one of the greatest victories in their history by defeating Real Madrid

What should have been a cakewalk for 9-time Champions League winners Real Madrid turned in to a nightmare, courtesy of a certain Andriy Shevchenko. The talismanic player, who went on to become a crucial part of the legendary AC Milan side of the early 2000’s, broke millions of Madrid hearts in both legs of the clash. While the Los Blancos managed to salvage a draw in the first leg at the Santiago Bernabeu as Predrag Mijatović cancelled out Shevchenko’s opener, they were left wondering what hit them in the second leg. Shevchenko scored twice for the Ukrainian side in the space of 17 minutes, en route to knocking out perhaps the greatest club to have played in the Champions League.

Real Madrid 1-1 Dynamo Kyiv (First Leg)

Dynamo Kyiv 2-0 Real Madrid (Return Leg)

 2. Real Madrid vs  AS Monaco (2003-04):

Real Madrid’s loanee Fernando Morientes scored against his parent club to knock them out of the Champions League

“I didn’t see one story in the papers that gave us a chance,” said AS Monaco’s Ludovic Giuly after helping his team pull off one the biggest upsets in the history of the elite tournament. Such was the predictability of this fixture due to the star-studded Real Madrid team which boasted the likes of Ronaldo, Zinedine Zidane, Luis Figo and Roberto Carlos. When Raul opened the scoring at the Stade Louis II in the second leg to make the aggregate 5-2 in favour of Real Madrid(they had demolished Monaco in the first leg at the Bernabeu), hardly anyone would have thought that it would be Monaco, and not Real Madrid, who will go through to the next round at the end of the final whistle. Guily netted on either side of the break along with Fernando Morientes (who, ironically, was on loan from Madrid) to send the famed Galacticos crashing out of the tournament on away goals.

Real Madrid 4-2 AS Monaco

AS Monaco 3-1 Real Madrid


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1. Deportivo La Coruña vs AC Milan:

Deportivo La Coruna defeated AC Milan to stage the greatest upset in the Champions League history

Arguably the greatest shocker in Champions League history, defending European champions AC Milan, having players like Andriy Shevchenko, Andrea Pirlo, Kaka, Paolo Maldini and Filippo Inzaghi were knocked out of the tournament in stunning fashion by a team who they had decimated 4-1 in the first leg. In the return leg at home, Deportivo wreaked havoc in the legendary Milan defense as Walter Pandiani, Juan Carlos Valeron and Albert Luque scored three in the first half itself to level the aggregate score at 4-4. Deportivo’s captain Fran piled further misery on Carlo Ancelotti’s men as he scored the winner in the 74th minute and the history books had got a result worth remembering.


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AC Milan 4-1 Deportivo La Coruña (First Leg)

Deportivo La Coruña 4-0 AC Milan (Second Leg)



Rajat Mohile

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