Unforgettable Upsets: The Greatest Shocks in Champions League Knockout Stage History

The knockout stages of the Champions League are widely regarded as the pinnacle of club football entertainment. It showcases Europe's most elite teams battling it out for the ultimate prize.

While Real Madrid stands as the most successful club in the tournament's history, aiming to secure their fifteenth title at Wembley in June 2024, they, like many others, have encountered their fair share of challenges along the way.

The Champions League has a knack for delivering unexpected surprises, with underdog teams from across Europe occasionally pulling off remarkable upsets in the latter stages of the competition. This article delves into eight of the most astonishing results witnessed in the history of the Champions League knockout rounds.

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Ranking factors

The list presented here ranks the most shocking Champions League knockout stage matches based on the disparity between the two teams' club coefficient rankings in the year of the tournament. It is important to note that all the matches included in this list occurred after the Champions League adopted its current format in 1992.

8. (15th) Porto vs Manchester United (3rd)

12 places apart in coefficient rankings

Porto's remarkable triumph in the 2004 Champions League, led by the young and talented manager Jose Mourinho, stands as one of the competition's most captivating stories. When Porto faced Sir Alex Ferguson's formidable Manchester United in the round of 16, most pundits expected an early exit for the Portuguese side, even after Benni McCarthy's brace secured a 2-1 victory in the first leg in Portugal.

In the return leg at Old Trafford, Paul Scholes' header seemed to be enough to send Manchester United through on away goals. However, in the dying moments of the match, McCarthy's powerful free-kick was mishandled by United goalkeeper Tim Howard, allowing Costinha to pounce on the rebound and secure Porto's place in the quarter-finals. Mourinho's ecstatic celebration saw him sprinting down the touchline, marking his memorable introduction to English football just a few months before he was appointed as the manager of Chelsea.

Can you believe it's exactly 15 years since Jose Mourinho ran down the Old Trafford touchline  pic.twitter.com/5NwyYl3xWP

— Football on TNT Sports (@footballontnt) March 9, 2019

7. (24th) Villarreal vs Inter Milan (7th)

17 places apart in coefficient rankings

In a remarkable achievement, Villarreal qualified for the Champions League just seven years after their first promotion to La Liga. Their journey led them to the quarter-finals, where they faced a formidable Inter Milan side that was on its way to securing the Serie A title convincingly that season. After a 2-1 defeat in the first leg at the San Siro, it seemed that the plucky Spanish team's adventure would come to an end.

However, in the second leg at El Madrigal, Villarreal displayed incredible resilience. Defender Rodolfo Arruabarrena's header in the 58th minute proved to be the decisive goal, allowing the Spanish side to triumph over the star-studded Inter team on away goals and progress to the semi-finals. This extraordinary run in their debut Champions League campaign came to an end in the semi-finals, where they were narrowly defeated by Arsenal across two legs.

6. (35th) Schalke vs Inter Milan (8th)

27 places apart in coefficient rankings

Inter Milan experienced an even more shocking upset in the Champions League five seasons later, despite entering the competition as defending champions. Under the management of Rafael Benitez, the Italian giants had struggled to qualify from their group and had already replaced Benitez with Leonardo by the time they incredibly staged a comeback to eliminate Bayern Munich in the round of 16.

Following their impressive victory, Inter Milan were considered strong favorites in their quarter-final clash against Schalke. However, they were left stunned as the German side dominated at the San Siro, securing a resounding 5-2 victory in the first leg. Ralf Rangnick's team made history by progressing to the semi-finals of the Champions League for the first time after also winning the second leg in Gelsenkirchen. However, their journey ended in the semi-finals, where they were convincingly defeated by Manchester United, with the final aggregate score favoring the Red Devils 6-1.

5. (46th) Dynamo Kyiv vs Real Madrid (16th)

30 places apart in coefficient rankings

Dynamo Kyiv, with Andriy Shevchenko leading their formidable attack, were once a regular presence in the latter stages of the Champions League. However, their chances of progressing past holders Real Madrid in the quarter-finals of the 1999 edition were doubted by many.

Nevertheless, the Ukrainian side proved their mettle by securing a 1-1 draw against Real Madrid at the Santiago Bernabeu. They followed up this impressive result with a 2-0 victory in the return leg, with Shevchenko scoring a second-half brace. This marked Dynamo Kyiv's third appearance in the semi-finals of the competition, narrowly missing out on progressing further as they were defeated by Bayern Munich over two legs. Despite their exit, Dynamo Kyiv's European journey showcased their strength and ability to compete with top-tier teams.

4. (31st) Ajax vs Real Madrid (1st)

30 places apart in coefficient rankings

Real Madrid, twenty years after their shocking defeat in the Ukrainian capital, experienced an even more astonishing loss in the Champions League knockout phase. As the reigning champions, Los Blancos anticipated an easy victory against Ajax, a team that hadn't won a knockout match in the competition for 22 years. The first leg seemed to confirm their dominance as they secured a 2-1 win in Amsterdam.

However, in a stunning turn of events at the Bernabeu, Erik ten Hag's Ajax executed an extraordinary comeback. Early goals from Hakim Ziyech and David Neres within 18 minutes flipped the scoreline in their favor. Dusan Tadic and Lasse Schone completed the job, ensuring a memorable 4-1 victory for Ajax in Madrid. Ajax continued their impressive run by defeating Juventus in the quarter-finals, but their own dreams were shattered in the semi-finals by Tottenham, who staged a miraculous comeback.

3. (37th) Roma vs Barcelona (3rd)

34 places apart in coefficient rankings

Following Barcelona's fifth Champions League triumph in 2015, they faced disappointment in the quarter-finals of the tournament in the subsequent two editions. However, they appeared to have turned the tide when they were drawn against Roma in the last eight, a seemingly favorable match-up. Barcelona dominated the first leg at the Nou Camp, winning 4-1.

Yet, just six days later, Eusebio Di Francesco's Roma staged an incredible comeback at the Stadio Olimpico. Despite the odds stacked against them, Roma turned the tie around, with Kostas Manolas' header eight minutes from time securing an improbable victory on away goals. The result propelled Roma to the semi-finals of the Champions League for only the second time in their history. Although they were narrowly beaten by Liverpool across two thrilling legs in the semi-finals, Roma's remarkable triumph over Barcelona remains an unforgettable moment in the competition's history.

2. (58th) Monaco vs Manchester City (11th)

47 places apart in coefficient rankings

In the 2016/17 season, Manchester City, under the management of Pep Guardiola in his first season, were expected to easily defeat Monaco in the Champions League round of 16. Monaco, ranked 47 places below City in the coefficient rankings, were seen as the underdogs. However, the French side proved their quality, boasting talented players who would soon attract attention from top European clubs, including a young Kylian Mbappe who was enjoying a breakout season.

In the first leg in Manchester, City narrowly emerged victorious in a thrilling encounter, winning 5-3. However, in the return leg in southern France, Monaco produced a stunning performance. Kylian Mbappe, Fabinho, and Tiemoue Bakayoko all found the back of the net, leading Monaco to a 3-1 victory and securing qualification to the next round on away goals. In the same season that Monaco clinched the Ligue 1 title ahead of PSG, they also reached the semi-finals of the Champions League for only the fourth time in their history, following a dominant quarter-final win against Borussia Dortmund.

1. (125th) APOEL vs Lyon (13th)

112 places apart in coefficient rankings

Undoubtedly, one of the greatest shocks in Champions League knockout football occurred in 2012 when APOEL achieved an extraordinary victory over Lyon in the round of 16. APOEL, a Cypriot side, had only qualified for the group stage of the competition once before the 2011/12 campaign. However, they defied the odds by defeating both Porto and Zenit to top Group G, setting up a clash with French giants Lyon in the round of 16.

In the first leg, Lyon managed a narrow 1-0 victory at home. But APOEL fought back in the return leg in Cyprus, repeating the 1-0 scoreline and forcing the match into a penalty shoot-out. APOEL displayed nerves of steel as they converted all of their penalties, while goalkeeper Dionysis Chiotis denied both Alexandre Lacazette and Michel Bastos from the spot, sealing the shoot-out win for APOEL. They became the first and only Cypriot side to reach the quarter-finals of the Champions League.

Unfortunately for APOEL, their remarkable journey ended in the next round against Real Madrid, who defeated them convincingly with an 8-2 aggregate score. Nonetheless, APOEL's achievement in reaching the quarter-finals will forever be remembered as a historic moment for Cypriot football in the Champions League.

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