The Champions League’s Biggest Upsets in Knockout Rounds
From shocking comebacks to underdog victories, the Champions League has seen some of the biggest upsets in football history. Relive the most unforgettable knockout round shocks.
The Champions League’s Biggest Upsets in Knockout Rounds
The UEFA Champions League is the ultimate stage for club football, where the best teams in Europe battle for the most prestigious title. While giants like Real Madrid, Barcelona, Bayern Munich, and Manchester United have dominated the competition, the tournament has also witnessed some of the biggest upsets in football history.
From underdogs eliminating tournament favorites to dramatic last-minute comebacks, the knockout rounds of the Champions League have given us some of the most unbelievable football moments. Let’s take a look at the biggest upsets in Champions League knockout history!
1. Deportivo La Coruña 4-0 AC Milan (2003-04 Quarter-Final)
AC Milan were the defending champions and one of the most dominant teams in Europe, boasting legends like Paolo Maldini, Andrea Pirlo, and Andriy Shevchenko. In the first leg, Milan crushed Deportivo La Coruña 4-1 at San Siro, seemingly ending the tie.
However, in the return leg, Deportivo produced one of the greatest comebacks in Champions League history, demolishing Milan 4-0 at the Riazor to win 5-4 on aggregate. It was a historic night for Spanish football and one of Milan’s worst collapses ever.
🔹 Key Moment: Deportivo scoring three goals in the first half, leaving Milan completely stunned.
2. AS Monaco 3-1 Real Madrid (2003-04 Quarter-Final)
Real Madrid’s Galácticos, featuring Zinedine Zidane, Ronaldo, and David Beckham, were clear favorites against a young AS Monaco side. Madrid won 4-2 in the first leg, and with players like Raúl and Figo, they seemed certain to advance.
However, Monaco, led by Didier Deschamps, stunned the football world by winning 3-1 in the second leg, knocking out the Spanish giants on away goals. A young Fernando Morientes, who was on loan from Madrid, scored against his parent club, completing the unbelievable upset.
🔹 Key Moment: Ludovic Giuly’s brace helped Monaco eliminate Real Madrid, proving that money doesn’t always guarantee success.
3. Chelsea 2-4 Barcelona (2017-18 Round of 16)
Chelsea had beaten Barcelona multiple times in past encounters, and after a 1-1 draw at Stamford Bridge, many expected them to challenge in the second leg. However, Barcelona, led by Lionel Messi, produced a masterclass at the Camp Nou, destroying Chelsea 3-0 and winning 4-1 on aggregate.
Chelsea had missed several key chances, and Messi capitalized on defensive errors, scoring twice and assisting Ousmane Dembélé in what became a statement performance.
🔹 Key Moment: Messi scoring just two minutes into the game, shattering Chelsea’s confidence early on.
4. Roma 3-0 Barcelona (2017-18 Quarter-Final)
Barcelona entered the second leg with a 4-1 lead after dominating Roma at the Camp Nou. Everyone believed the tie was over, but Roma had other plans. At the Stadio Olimpico, Edin Džeko, Daniele De Rossi, and Kostas Manolas scored in a miraculous 3-0 victory, eliminating Barcelona on away goals.
Barcelona’s shocking collapse remains one of the biggest upsets in Champions League history, proving that no lead is ever safe in football.
🔹 Key Moment: Manolas’ header in the 82nd minute, sending the home fans into absolute chaos.
5. Ajax 3-2 Real Madrid (2018-19 Round of 16)
Real Madrid, the three-time defending champions, faced a young Ajax team led by Matthijs de Ligt, Frenkie de Jong, and Dusan Tadić. After winning the first leg 2-1 at the Santiago Bernabéu, many believed Madrid would comfortably progress.
However, in the second leg, Ajax humiliated Madrid 4-1 at the Bernabéu, eliminating the Spanish giants 5-3 on aggregate. It was one of the most stunning performances by an underdog in Champions League history.
🔹 Key Moment: Dusan Tadić’s magical performance, running the show with a goal and two assists.
6. Tottenham 3-2 Ajax (2018-19 Semi-Final)
After eliminating Real Madrid and Juventus, Ajax looked destined for the final, holding a 3-0 aggregate lead at halftime in the second leg against Tottenham. But Lucas Moura produced one of the greatest individual performances in Champions League history, scoring a hat-trick in the second half, including a 96th-minute winner, to complete the stunning comeback.
Ajax’s dream run ended in heartbreak, while Tottenham advanced to their first-ever Champions League final.
🔹 Key Moment: Lucas Moura’s last-second goal, sending Tottenham to the final in dramatic fashion.
7. Bayern Munich 1-3 Villarreal (2021-22 Quarter-Final)
Bayern Munich, one of the biggest clubs in Europe, were clear favorites against Villarreal, a club with far less financial power. However, Unai Emery’s side shocked the world, winning the first leg 1-0 and then drawing 1-1 in the second leg, eliminating the German giants 3-1 on aggregate.
🔹 Key Moment: Samuel Chukwueze’s late equalizer, sealing Villarreal’s place in the semi-finals.
8. Manchester United 1-2 FC Basel (2011-12 Group Stage)
Manchester United were runners-up in the previous season and were expected to cruise through their group stage. However, they failed to beat FC Basel, suffering a shocking 2-1 defeat, which eliminated them from the tournament.
It was one of the biggest group-stage upsets in recent memory, proving that even the biggest clubs aren’t immune to shock exits.
🔹 Key Moment: Alexander Frei’s goal, confirming United’s early exit.
Conclusion: The Champions League – The Tournament of Surprises
The Champions League has always been unpredictable, where underdogs can triumph and giants can fall. Whether it’s last-minute goals, shocking collapses, or tactical masterclasses, football fans continue to witness historic upsets that define the beauty of the sport.
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