Top 10 Knockout Round Upsets in Champions League History

Footballing tournaments such as the World Cup, the European Championships and the UEFA Champions League always leave open a window of opportunity for improbable results to become possible. In the case of the latter, it’s a much more unpredictable tournament than you’d think, despite the best teams in the world squaring off against some of Europe’s minnows. However, results in this tournament have never been particularly cut and dry. In this top 10 list, we will be counting down the biggest upsets seen in the knockout round of the Champions League in the tournament’s history.

Several of these upsets involve the same clubs: Chelsea feature three times on the winning end of the upset, while Barcelona, Real Madrid, Bayern Munich and AC Milan all feature twice each on the losing end. It takes a pretty superb performance for the underdog club to topple Europe’s world-beaters, and the games profiled on this list are among the best examples seen in the Champions League’s knockout rounds.

Some of these matches involved teams overcoming almost insurmountable deficits to progress to the next round, while other matches were Champions League finals that involved teams having to go to the penalty shootout to decide the winner – at least once after a thrilling lead was cancelled out by the time the 90 minutes were up.

Regardless, these matches have provided stories that fans of the teams who profited from those upsets will never forget, and also made heroes out of players such as Thierry Henry, Didier Drogba and Ole Gunnar Solskjær. In short, the Champions League is far from predictable, and these 10 matches are proof of that – just ask the teams listed here. Let’s take a look at the knockout round matches of the Champions League that turned the heads of the footballing world.

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10 Chelsea 4-1 Napoli (2012)

Under the brief management of Roberto Di Matteo, Chelsea’s hopes in the 2011-12 Champions League looked all but dashed against Napoli of the Serie A, after losing 3-1 to the Italian outfit in the first leg of the Round of 16. However, the second leg at Stamford Bridge would see a dramatically different outcome in favour of the Blues: Didier Drogba and John Terry opened the scoring at 2-0, though Chelsea were again in hot water when Gökhan Inler cut the deficit in half for Napoli in the 55th minute. Luckily for Chelsea, a Frank Lampard penalty and an extra time goal by Branislav Ivanović were enough to complete a dramatic comeback leading up to Chelsea’s eventual Champions League victory that season (more on that later).

9 Chelsea 2-2 Barcelona (2012)

Following the comeback against Napoli, Chelsea faced much more fearsome opponents in Barcelona in the quarterfinals. A 1-0 victory at Stamford Bridge courtesy of a Didier Drogba goal was hardly a reassuring lead, and the odds against them keeping their lead at the Nou Camp were small. Furthermore, John Terry would get sent off in the 37th minute, reducing Chelsea to 10 men for the rest of the match. However, Chelsea again caused an upset after Sergio Busquets and Andres Iniesta put the Blaugrana up 2-0, when Ramires and Fernando Torres equalized before the final whistle blew to seal progression to the semifinals for the Blues.

8 AC Milan 4-0 Barcelona (1994)

With a lineup boasting players such as Hristo Stoichkov, Ronald Koeman, Romario and Michael Laudrup, it would have been absolutely fair to assume Barcelona would have been good enough to win the 1994 Champions League in convincing fashion. However, AC Milan had other plans: two goals from Daniele Massaro before the end of the first half put the Rossoneri up 2-0 before Dejan Savićević and Marcel Desailly added two more by the 58th minute. It would be enough to see Milan take home the Champions League trophy in style. The same season, Milan would also win their third consecutive Scudetto.

7 Arsenal 1-0 Real Madrid (2006)

Against a Real Madrid team still deep in the midst of their Galacticos era, the odds of Arsenal winning this round of 16 match were debatable at best. However, Real simply could not get anything going in terms of goals: a goal from Thierry Henry just after the start of the second half in the first leg at the Bernabeu was enough to send Real packing, as the return leg only resulted in a 0-0 draw. Even more impressive is the fact that the Gunners defense was particularly young, with Kolo Touré the oldest member of the Arsenal defense corps at only 24.

6 APOEL 1-0 Lyon (2012)

Although Lyon weren’t necessarily a world-beating team by any stretch in 2012, they were still strong enough to beat a minnow club from Cyprus convincingly for all intents and purposes. However, that was not to be in the 2012 Champions League round of 16: a goal from APOEL’s Gustavo Manduca in the ninth minute cancelled out an Alexandre Lacazette goal from the first leg, and extra time proved fruitless in terms of finding a winner. Thus, the game went to penalties: APOEL converted all four of their kicks, while two misses from Lacazette and Michel Bastos were enough to bring the Cypriots to their first ever Champions League quarterfinal appearance.

5 Monaco 3-1 Real Madrid (2004)

During the 2003-04 season, Real Madrid seemed like a team that had all the pieces needed for domestic and European glory: Zidane. Figo. Beckham. Ronaldo. Raul. A number of the world’s elite footballers at that time plied their trade at the Bernabeu, and with a 4-2 victory in the first leg of the Champions League quarterfinals against Monaco, it seemed like progression to the last four wasn’t going to be a stretch for Los Merengues. Luckily for Monaco supporters, that’s not how it panned out: a 3-1 victory at home thanks to goals from Ludovic Giuly (twice) and former Real Madrid player Fernando Morientes sent the Monegasque outfit to the semis.

4 Deportivo la Coruña 4-0 AC Milan (2004)

In that same quarterfinal round, Deportivo la Coruña looked all but finished following a 4-1 loss to AC Milan in the first leg at the San Siro. However, the return leg in Spain proved far more fruitful for Deportivo than they probably ever imagined: goals from Walter Pandiani, Juan Carlos Valerón, Albert Luque and Fran Gonzalez helped the Galician side overturn their intimidating deficit and sent them to the Champions League semifinals. However, it was here that their luck would run out: Deportivo would lose 1-0 to Porto in the semis, who were coached by a then-unheralded Jose Mourinho.

3 Chelsea 1-1 (4-3 penalties) Bayern Munich (2012)

The stage was set – literally. With the 2012 Champions League final being held at the Allianz Arena in Munich, and with a cast of players that was nothing short of star-studded, Bayern Munich seemed like a foregone conclusion to win the Champions League trophy on home soil against Chelsea. However, despite scoring chance after scoring chance – outshooting Chelsea 35 to 9 – only Thomas Müller could convert in the 83rd minute for Bayern, until he was cancelled out five minutes later by Didier Drogba. The match would eventually go to penalties, where misses from Ivica Olić and Bastian Schweinsteiger would cause despair and disappointment for Munich fans and send Chelsea supporters into unexpected euphoria, giving the Blues their maiden Champions League title.

2 Manchester United 2-1 Bayern Munich (1999)

With stoppage time just about to begin in the 90th minute, Bayern Munich seemed as if they had won the Champions League trophy with a 1-0 lead thanks to Mario Basler in the sixth minute of the match. However, such slim leads can be curses much more often than blessings, and Manchester United took advantage of this at the 11th hour – just as Bayern-coloured ribbons had already been attached to the trophy in anticipation for it to be awarded to them – with goals from Teddy Sheringham and Ole Gunnar Solskjær both coming in stoppage time to seal the trophy for the Red Devils in Peter Schmeichel’s last game between the sticks for United.

1 Liverpool 3-3 (3-2 on penalties) AC Milan (2005)

By the time the second half was about to start during the 2005 Champions League final in Istanbul, AC Milan couldn’t have been faulted for thinking they had already won the trophy. A goal from Paolo Maldini within the first minute as well as two more from Hernán Crespo had given the Rossoneri a convincing 3-0 lead. After Liverpool changed their formation at the half with three defenders and five midfielders, it would prove to be a gamble that paid off: goals from Steven Gerrard, Vladimír Šmicer and Xabi Alonso would make for a thrilling comeback for Liverpool – a comeback they would complete in the penalty shootout with Šmicer, Dietmar Hamann and Djibril Cissé converting for the Reds to win them the trophy.

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