Top 10 Biggest Champions League Upsets Of All Time
This list features some of Europe’s biggest clubs like Inter, Real Madrid, and Barcelona, the most surprising small-team comebacks, and some of the biggest Champions League upsets since the infamous 1992/93 season.
If you’re a fan of big soccer clubs like Inter, Real Madrid, and Barcelona, at least some of these are guaranteed to make your blood boil!
10-6
10. Deportivo La Coruña 5–4 AC Milan (2003/04)
After taking over as AC Milan’s head coach in 2001, Carlo Ancelotti led the club to its sixth Champions League win in the 2002/03 season. However, the next year’s Champions League quarter-finals would bring the team’s biggest upset since 1993.
AC Milan started their 2003/04 run in full force, winning their 17th Scudetto at the time and later entering the second leg of the Champions League quarter-finals with a 4–1 advantage against Deportivo La Coruña.
Although Deportivo was participating in the Champions League for the fourth consecutive year, the Spanish team had never made it to the league semi-finals before.
It seemed like all the cards were stacked in Milan’s favor, yet Deportivo made a stunning comeback. Already leading with three goals before halftime, they won the second leg 4–0 against the Italians.
With this performance, Deportivo won the quarter-finals 5–4 on aggregate, blocking AC Milan’s entry into the semi-finals.
9. Villarreal 2–2 Inter Milan (2005/06)
Although the 2005/06 season saw Villareal’s first appearance in the UEFA Champions League, the Spanish team beat all expectations. Villareal knocked Inter Milan out of the quarter-finals after a tense 2–2 draw in the aggregate and winning on away goals.
This came as a surprise after Inter’s successful streak for the season. In 2005/06, Inter Milan won their 14th Serie A title and went on to lift the Supercoppa for the second time since 1990.
Their run to the Champions League quarter-finals also saw them lose only one match (a 2–0 defeat to Porto in the group stage). In the round of 16, Inter Milan beat Ajax with a 3–2 score on aggregate.
By comparison, Villareal had a streak of zero losses prior to their match against Inter in the first leg of the quarter-finals. However, the Champions League newcomers only had two decisive wins for the season (1–0 against Benfica and 1–0 against Lille).
8. Maccabi Haifa 2-0 Juventus (2022/23)
For number eight on our list, we have one of the more recent Champions League shocks—a defeat that marked one of Juventus’s worst seasons.
Although Juventus had a rocky start to 2022, Maccabi Haifa’s 2–0 win was still a huge surprise to many fans. Despite Juventus’s previous 3–1 win against the Israeli team, this loss was the beginning of the end for the Italian giant.
After two prior losses to Benfica and PSG, Maccabi Haifa’s win pushed Juventus near the edge in the group stage, prompting harsh criticism for Massimiliano Allegri’s managerial downturn. With the next 3–4 loss to Benfica, Juventus’s crash out of the group stage was a first in nine years.
The loss to Maccabi Haifa was all the more surprising, given this was the team’s third appearance in the UEFA Champions League group stage and their first win against Juventus after two previous losses in the 2009/10 season.
7. Galatasaray 3–3 Manchester United (2023/24)
Man United might have been ranked as the 10th-best soccer team in early 2023, but the three-times Champions League winner suffered one of its most stinging blunders this season.
If their 3–2 loss to Galatasaray wasn’t enough, their subsequent 3–3 draw against the Turkish team might have been Man United’s biggest Champions League upset to date.
Despite Manchester United’s powerful start, which had them leading with 2 goals at 18 minutes, Ziyech and Kerem Aktürkoğlu’s goals in the second half helped Galatasaray even the score, ending the match with a draw.
This match marked the Brits’ fourth winless game in the group stage before their upcoming match against Bayern, which many fans saw as a moment of no return.
Worse yet, this event saw Man United concede its 14th goal in five matches, reaching the bottom of Group A and setting an embarrassing record for most goals conceded by an English team in one single group stage.
6. Schalke 7–3 Inter Milan (2010/11)
Inter Milan’s 2009/10 Champions League win was still fresh for many fans, but the 2010/11 season was already tense for Inter.
The Italian team kicked off with a draw against FC Twente and later suffered two group-stage losses: 3–1 to Tottenham Hotspur and 3–0 to Werder Bremen. However, things looked up when Inter beat Bayern on away goals to enter the quarter-finals.
Still, the three-times Champions League winner struggled against Schalke. By halftime, the score was 2–2, though Inter ended up losing 5–2 in the first leg. The second match saw another 2–1 loss to Schalke, despite Inter’s aggressive game with 15 total attempts.
With an aggregate score of 7–3, Schalke beat Inter Milan and made the Champions League semi-finals for the first time, though the German team would later lose 4–1 to Manchester United.
5–1
5. Marseille 1–0 AC Milan (1992/93)
The 1992/93 season was a big chapter in European soccer history for two reasons. First, it marked the event’s rebranding from the ‘European Cup’ to the now iconic ‘Champions League.’
Secondly, the cup concluded with one of the most shocking and controversial wins to date, and the match became one of the biggest Champions League upsets in history.
Milan was set to make history, becoming Europe’s fourth club to be awarded a permanent league trophy. They had already lifted the European Champion Clubs’ Cup four times up to the ‘92 season.
With legendary players like Marco van Basten and Paolo Maldini within its ranks, Milan’s victory seemed guaranteed.
This made the turn of events all the more shocking when Marseille beat AC Milan 1–0 in the final and became the first French team to win the UEFA Champions League.
Marseille’s win against AC Milan is still upsetting many fans today, especially considering the resurfacing of Marseille’s bribery and doping scandals in recent years.
4. Monaco 5–5 Real Madrid (2003/04)
Even before Cristiano Ronaldo joined in 2009, Real Madrid had long been a force to be reckoned with. The club’s solid reputation made Monaco’s unforeseen comeback one of the biggest upsets in European soccer history.
In the 2003/04 season, the Spanish club already had six European Champion Clubs’ Cups and three UEFA Champions League titles under its name. In fact, Real Madrid was the first team to win five consecutive editions from 1956–1960 and the first to be awarded a permanent trophy.
With zero losses up to the second leg of the Champions League quarter-finals and a 4–2 win against Monaco in the first leg, few expected the French team’s 3–1 victory against Madrid in early April.
After a 5–5 draw on aggregate, Monaco won on away goals and knocked Real Madrid out of the quarter-finals. Ironically, their team’s top scorer for the season, Fernando Morientes, had only recently joined the team as a loan from Real Madrid.
3. Monaco 6–6 Manchester City (2016/17)
After a series of ups and downs in the previous season, Manchester City appointed Pep Guardiola as its new head coach. With the former Barcelona and Bayern star taking over, the 2016/17 season was expecting major upcoming events for Man City.
But their Champions League loss to Monaco wasn’t on the list, especially after their previous win at home against Barcelona in the group stage.
Man City got off to a good start in the first leg of the Round of 16. After a 5–3 win against Monaco, it seemed like City had the upper hand. However, Monaco was in very good form in the 2016/17 season, ranking fifth place alongside Juventus for total goals scored in the league.
Monaco led 2–0 before halftime in the second leg, and Tiémoué Bakayoko’s goal 77 minutes in ended the Round of 16 tie with a 6–6 aggregate score.
With a win on away goals, Monaco blocked Manchester City from reaching the quarter-finals. This marked not only a huge comeback for Monaco but also the first time in Guardiola’s managerial career that he failed to make the semi-finals.
2. Roma 4-4 Barcelona (2017/18)
AS Roma might have been making its tenth appearance in the Champions League, but Barcelona had already lifted the cup five times, most recently in the 2014/15 season.
Barcelona’s 2017/18 season was already a resounding success. With just one loss, they won both the La Liga and Copa del Rey. Unfortunately, their defeat to Roma in the quarter-finals would make for an unexpected conclusion.
After a strong start at home, the Spanish giants kept their rhythm in the Champions League, crushing the group stage and round of 16 with zero matches lost. The team was in top shape for the season, with Lionel Messi ranking second in the 2017 Ballon d’Or.
Later, Barcelona beat Roma 4–1 in the first leg. It seemed like Barcelona’s entry into the semi-finals was a given. But the Italian team made one of the greatest comebacks in the League’s history.
The second leg ended with Barcelona losing 3–0 to Roma (with a 4–4 aggregate score), and Roma winning on away goals, kicking Barcelona out of the race.
1. Lyon 3-1 Manchester City (2019/20)
Although Manchester City hadn’t won a Champions League title before, their recent home success and impressive start in the 2019 season made them a crowd favorite to win this time around.
Man City ranked #1 in the 2019 soccer power index, so the hopes were higher than ever. Given their run to the quarter-finals, their defeat to Lyon was a huge shock.
Since starting his tenure at Manchester City, Pep Guardiola established himself as the club’s most prolific coach. In the 2017/18 season, his team went on to establish a Premier League record for the most consecutive victories after winning 18 games in a row.
In the 2019/20 season, Man City lifted its third consecutive English League Cup under Guardiola and entered the Champions League quarter-finals with 0 losses and a 4–2 victory on aggregate against Real Madrid.
But despite beating the Spanish giants, Manchester City lost to Lyon in the first leg of the quarter-finals. The English team was in possession of the ball for most of the game and had nearly three times as many attempts as Lyon, but in the end, they suffered a 3–1 loss to their French rival.
Which Club Has The Most UEFA Champions League Wins?
As of 2023, Real Madrid dominates the Champions League, ranking #1 for the most title wins, total games played, and total appearances in league finals.
Last season, Real Madrid had 14 Champions League wins, twice as many as its closest runner-up, AC Milan. According to UEFA’s official website, Real Madrid is also the club with the most consecutive Champions League wins, recorded between 2016 and 2018.
From 1955–2023, Real Madrid played 476 Champions League games, more than any other European soccer giant, including Bayern Munich and Barcelona.
As of 2023, Real Madrid had also played in 17 Champions League finals, making it among Europe’s top three clubs for most consecutive league finals appearances.
With Real Madrid’s semi-final match against Bayern coming up soon, we might see the Spanish club extend its triple record this season.
What Was The Biggest Champions League Win?
According to UEFA, Real Madrid and Liverpool are currently the record holders for the overall biggest goal margin victories in the Champions League.
Liverpool set this record first, with an 8–0 win against Beşiktaş in the 2007 season group stage. Real Madrid equaled this feat in 2015 with an 8–0 group stage match against Malmö.
The second-biggest goal margin in Champions League history is 7–0, and it goes to multiple teams. Most notably, Bayern was the first team to win 7–0 twice in the round of 16—first, against Basel in 2012 and later, against Shakhtar Donetsk in 2015.
However, the biggest final win in the Champions League goes to AC Milan’s 4–0 victory against Barcelona in 1994. This is still the biggest goal margin recorded in the finals, and went down as one of the most memorable wins in Champions League history.
What’s The Best Champions League Player Of All Time?
According to UEFA’s all-time stats and rankings, Cristiano Ronaldo is the most prolific player in Champions League history. To date, he’s played in 187 matches and scored 141 goals, having a 12-goal edge over Lionel Messi at #2.
Ronaldo also has the most assists, 42 as of last season, and was ranked the top goalscorer for six consecutive Champions League seasons, from 2012/13 to 2017/18.
But even beyond his impressive Champions League figures, Cristiano Ronaldo has managed many amazing feats throughout his career so far, including:
- 5x Ballon d’Or wins (in 2008, 2013–2014, and 2016–2017)
- 4x UEFA Best Player In Europe titles (in 2008, 2014, and 2016–2017)
- 8x Player Of The Year titles (in 2006–2008, 2012–2014, and 2018–2021)
- 14x Footballer Of The Year titles (most notably throughout 2015–2020 in Portugal and Italy)
- 19x Top Goal Scorer titles (including in 2014/15, when he scored 48 goals in La Liga)
Given his multiple records, we can safely say Ronaldo is not only the best player in Champions League history but one of the best soccer players in the world.
Who’s The Best Champions League Coach Of All Time?
As of the 2023/24 season, Carlo Ancelotti is the best coach in Champions League history. According to UEFA, Ancelotti has been in charge of and won the most UEFA Champions League games so far, even surpassing Sir Alex Ferguson.
In April 2024, Carlo Ancelotti had 201 games played and 114 wins in the Champions League. Pep Guardiola is his closest contender for the #1 spot, boasting 109 wins after 169 games played.
Since 2022, Carlo Ancelotti’s also set the latest record for the most UEFA Champions League titles won, which currently stands at four.
Second place goes to Pep Guardiola and Zinédine Zidane, both boasting three wins each. However, with Manchester City out of the league this season, we won’t see Guardiola equaling Ancelotti’s records this year.
Concluding Thoughts
The UEFA Champions League has provided countless unexpected outcomes and dramatic moments through the years. Even the biggest clubs like Real Madrid and Manchester City aren’t safe from these shocking defeats, and Man City’s 2019/20 loss to Lyon goes to prove it.
But we’re just scratching the surface. This list included the biggest Champions League upsets where bigger clubs crashed out of the race, though surprising defeats abound even without crowd favorites exiting the league. Barcelona’s 2–3 loss to Antwerp in this season’s group stage is just one such example.