Biggest Champions League Upsets of All Time — Shocks That Shook Europe

⭐ UCL Upsets · 40 Questions · Updated May 2026

The Champions League promises the continent’s elite clubs — but it has repeatedly delivered its greatest shocks when the underdogs refuse to read the script. From Istanbul’s Miracle to Deportivo La Coruña’s impossible comeback against AC Milan, these are the moments that defined European football. Test your knowledge with these 40 biggest Champions League upset trivia questions. Also explore our UCL all-time records quiz and our guide to Real Madrid’s 15 UCL titles.

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Famous UCL Upsets — Easy (Questions 1–12)

Easy

1. Q: In the 2005 UCL Final, Liverpool were 3-0 down at half-time to AC Milan. What was the final score?
   A: 3-3 after extra time — Liverpool won on penalties. Steven Gerrard, Vladimir Smicer, and Xabi Alonso scored three goals in six second-half minutes to level the match. This is known as the “Miracle of Istanbul.”
2. Q: Which team did Chelsea beat in the 2012 UCL Final as clear underdogs, having trailed Barcelona in the semi-finals?
   A: Bayern Munich — Chelsea beat them on penalties in Munich, at Bayern’s own stadium. Chelsea had only reached the final after Didier Drogba’s stoppage-time header made it 1-1 in normal time.
3. Q: Ajax eliminated which two giants in the 2018-19 UCL knockout rounds to reach the final?
   A: Real Madrid (4-1 in the Round of 16 second leg) and Juventus (3-2 on aggregate in the quarter-finals). In the semi-final they led Tottenham 3-0 at half-time in the second leg before a devastating 3-3 collapse (Tottenham through on away goals).
4. Q: Liverpool came back from 3-0 down to beat Barcelona 4-0 in the 2019 UCL semi-final second leg. What was notable about the fourth goal?
   A: Trent Alexander-Arnold took a quick corner while Barcelona were not set — catching the entire defence off guard. Divock Origi tapped in, and the goal became one of the most celebrated moments in UCL history.
5. Q: Which German club reached the 2013 UCL Final as underdogs and lost to Bayern Munich in the first “Der Klassiker” final at Wembley?
   A: Borussia Dortmund — they lost 2-1, with an Arjen Robben winner in extra time.
6. Q: Leicester City reached the UCL quarter-finals in 2016-17. Who knocked them out?
   A: Atletico Madrid — winning 2-1 on aggregate in a tight two-legged tie. Leicester’s run as 5000-1 Premier League outsiders was remarkable.
7. Q: In 2004, Deportivo La Coruña trailed AC Milan 4-1 from the first leg of their UCL quarter-final. What happened in the second leg?
   A: Deportivo won 4-0 — completing one of football’s most remarkable comebacks to go through 5-4 on aggregate, knocking out one of Europe’s powerhouse clubs.
8. Q: Manchester United famously beat Bayern Munich in the 1999 UCL Final with two stoppage-time goals. What was the score at the 90th minute?
   A: 1-0 to Bayern Munich — Mario Basler had scored in the 6th minute. Teddy Sheringham (91′) and Ole Gunnar Solskjær (93′) won it 2-1 for United.
9. Q: Which club beat Real Madrid and Juventus to reach the UCL semi-finals in 2020-21?
   A: Chelsea — who knocked out both Atlético Madrid and Porto before eliminating Real Madrid in the quarter-finals and then Manchester City in the semi-finals, going on to win the title.
10. Q: Monaco reached the UCL semi-finals in 2016-17, beating Manchester City in the Round of 16. Who was their teenage star striker?
    A: Kylian Mbappé — whose performances prompted his world-record move to Paris Saint-Germain the following summer.
11. Q: Steaua Bucharest won the 1986 European Cup as significant underdogs. Who did they beat in the final?
    A: Barcelona — Steaua won on penalties after a goalless draw in Seville. They remain the only Romanian club to win the European Cup/Champions League.
12. Q: Nottingham Forest won the European Cup in 1979 and 1980 — what was remarkable about their status at the time?
    A: They had only been promoted to the First Division in 1977 — winning the league title in 1977-78 and then back-to-back European Cups under Brian Clough in an unprecedented rise from the second tier.

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UCL Upsets — Medium (Questions 13–28)

Medium

13. Q: In 2018-19, Ajax’s second-leg win against Juventus was decisive. What was the aggregate score?
    A: 3-2 on aggregate — Cristiano Ronaldo scored for Juventus in the first leg, but Ajax won the second leg 2-1 in Turin, with Matthijs de Ligt’s header sealing one of the modern era’s great upsets.
14. Q: In 2004-05, Chelsea were eliminated by Liverpool in the UCL semi-final despite being the English league leaders. What settled it?
    A: Luis García scored a controversial “ghost goal” — the ball appeared not to have fully crossed the line, but the goal was awarded. Liverpool advanced on that disputed finish.
15. Q: Malaga reached the UCL quarter-finals in 2012-13 before being eliminated in controversial circumstances by Borussia Dortmund. What happened?
    A: Malaga led deep into stoppage time before two late Dortmund goals (93′ and 94′) completed a 3-2 aggregate win in one of the UCL’s most dramatic turnarounds.
16. Q: Porto, under José Mourinho, won the UCL in 2004. Which English club did they eliminate on the way?
    A: Manchester United — Porto beat United 3-2 on aggregate in the Round of 16 before going on to beat Monaco 3-0 in the final in Gelsenkirchen.
17. Q: Real Madrid completed one of football’s greatest comebacks against Manchester City in the 2022 UCL quarter-finals. What was the aggregate score?
    A: 6-5 on aggregate — City led 5-3 after the first leg. Real Madrid scored three times in the final 10 minutes of the second leg, with Rodrygo scoring twice in stoppage time and Benzema completing the comeback in extra time.
18. Q: In 2016, Atletico Madrid eliminated Barcelona in the UCL quarter-finals. What was their defensive achievement across both legs?
    A: Atletico kept two clean sheets — winning 2-0 on aggregate, shutting out arguably the world’s greatest attacking trio (Messi, Suárez, Neymar) in a defensive masterclass.
19. Q: Celtic beat Barcelona 2-1 in a UCL group stage match in 2012-13. Why was this considered a massive upset?
    A: Barcelona were the reigning UCL champions with Messi, Xavi, Iniesta, and other world-class players at their peak. Celtic Park’s atmosphere played a significant role in one of the competition’s great group stage shocks.
20. Q: In 2010-11, Villarreal reached the UCL semi-finals. Which clubs did they eliminate on their run?
    A: Celtic (group stage), Porto (round of 16), and Bayern Munich (quarter-finals) before losing to Manchester United in the semi-finals — the furthest the Yellow Submarine had ever reached.
21. Q: CSKA Moscow eliminated Real Madrid from the UCL group stage in 2009-10. Why was this particularly embarrassing for Madrid?
    A: Real Madrid had just signed Cristiano Ronaldo and Kaká for combined world-record fees exceeding €150 million — yet were knocked out of the group stage by CSKA, highlighting that investment alone doesn’t guarantee UCL success.
22. Q: In 2016, Atletico Madrid beat Bayern Munich in the UCL semi-finals to reach the final. How did the tie finish?
    A: 2-2 on aggregate — Atletico won 1-0 in Munich in the first leg, then drew 2-1 at home when Bayern scored twice. Atletico advanced on away goals.
23. Q: Liverpool’s 2018 semi-final second leg against Roma saw Roma score four goals at home. What was the overall aggregate?
    A: Liverpool won 7-6 on aggregate — Roma won the second leg 4-2 in Rome, but Liverpool’s two away goals (scored in Rome) meant they went through on aggregate.
24. Q: In 2020, Paris Saint-Germain reached their first UCL Final in the COVID-era tournament held in Lisbon. Who beat them?
    A: Bayern Munich — who won 1-0 in the final thanks to a goal from Kingsley Coman, ironically a former PSG player.
25. Q: Which English club reached the UCL Final in 2019 for the first time in their history after overturning a 1-0 deficit against Ajax?
    A: Tottenham Hotspur — Lucas Moura scored a hat-trick in the second leg to win 3-2 and reach the final on away goals. They lost the final 2-0 to Liverpool.
26. Q: Sheriff Tiraspol from Moldova caused a massive UCL group stage upset in 2021-22. Who did they beat in their most famous victory?
    A: Real Madrid — Sheriff won 2-1 at the Santiago Bernabéu in one of the biggest group stage upsets in Champions League history. They had also beaten Shakhtar Donetsk in qualifying.
27. Q: Valencia reached two consecutive UCL Finals in 2000 and 2001 — who beat them in each?
    A: Real Madrid beat them 3-0 in the 2000 final; Bayern Munich beat them on penalties in the 2001 final (1-1 after extra time). Valencia became the only club to lose two consecutive UCL Finals.
28. Q: Atalanta made their UCL debut in 2019-20 and nearly produced a stunning upset in the quarter-finals. Who scored twice in injury time to deny them?
    A: PSG — Eric Maxim Choupo-Moting scored the 93rd-minute winner after Atalanta had led 1-0 deep into stoppage time. PSG went on to reach the final before losing to Bayern.

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UCL Upsets — Hard (Questions 29–40)

Hard

29. Q: In 1999, Manchester United became the second English club to win the continental treble. Who was the first British club to win a treble including the European Cup?
    A: Celtic — in 1967, under Jock Stein, they became the first British club to win the European Cup, and also won the Scottish League and Scottish Cup — the first treble in British football history.
30. Q: Real Madrid’s 2022 UCL run was described as the greatest in modern history. How many times did they come from behind in the knockout stages?
    A: Four times — they overturned deficits against PSG (Benzema hat-trick in the 2nd leg), Chelsea, Manchester City (Rodrygo’s last-gasp goals), and survived Liverpool’s chances in the final. Each round involved late drama.
31. Q: In 2023-24, which club reached the UCL Final as significant underdogs having had a rocky Bundesliga season?
    A: Borussia Dortmund — they excelled in the UCL despite mid-table Bundesliga form, reaching Wembley before losing 2-0 to Real Madrid.
32. Q: In the 2019-20 UCL played behind closed doors due to COVID-19, PSG beat Atalanta with two injury-time goals. Who scored the winner?
    A: Eric Maxim Choupo-Moting — in the 93rd minute, after Atalanta had led 1-0 deep into stoppage time. PSG’s comeback was one of the strangest results of the pandemic-era tournament.
33. Q: Liverpool’s 2019 comeback against Barcelona featured a substitute who scored twice in two minutes, later joining Barcelona. Who was he?
    A: Georginio Wijnaldum — he came off the bench at half-time with Liverpool 3-0 down on aggregate and scored twice (54′, 56′) before Origi’s famous fourth. Wijnaldum joined Barcelona on a free transfer in 2021.
34. Q: The 1984 European Cup Final between Roma and Liverpool was played at which significant stadium?
    A: The Stadio Olimpico in Rome — Roma’s own home ground. Despite the partisan crowd, Liverpool won on penalties, one of football’s most remarkable instances of an away team playing a “home” final.
35. Q: Deportivo La Coruña beat AC Milan 4-0 in 2004. Who scored the goals for Deportivo?
    A: Walter Pandiani (2), Albert Luque, and Fran — four different scorers completing the 5-4 aggregate comeback against AC Milan, who had won the Champions League the previous year.
36. Q: Ajax’s 2018-19 UCL run was extraordinary because they eliminated two former champions. What made it even more remarkable?
    A: Ajax simultaneously had the youngest squad in the competition and later sold the core of the team that summer — de Ligt to Juventus, de Jong to Barcelona, Ziyech to Chelsea. Their run produced over €300m in transfer revenue while reaching the final.
37. Q: In the 2001 UCL Final, Bayern Munich beat Valencia on penalties. What was unusual about the match’s two goals?
    A: Both goals were own goals — Stefan Effenberg scored Bayern’s winner in normal time but it was an own goal, and the match finished 1-1 after extra time. Penalties settled a final where neither side scored a “proper” goal.
38. Q: Which Greek club caused major upset runs in UCL qualifying during the 2010s, twice reaching the group stage against the odds?
    A: PAOK Thessaloniki — they made several qualifying runs and faced major European clubs, while Olympiacos (AEK Athens in later seasons) appeared in multiple group stages, representing Greece’s limited but genuine UCL presence.
39. Q: In 2004-05, which club from the Netherlands eliminated Arsenal in the UCL group stage despite being considered significant underdogs?
    A: PSV Eindhoven eliminated Arsenal from the last 16 on away goals (1-1 on aggregate) — PSV had also beaten Arsenal in the same group stage run, one of the Dutch club’s better UCL campaigns of the 2000s.
40. Q: Kaiserslautern were promoted from the Bundesliga second tier in 1996-97, won the Bundesliga title in 1997-98, and then entered the Champions League. What happened?
    A: They were eliminated in the group stage of the 1998-99 UCL — but their presence as freshly promoted Bundesliga champions competing in the Champions League remained one of German football’s most extraordinary stories.

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How Did You Score?

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Frequently Asked Questions

What is the biggest upset in Champions League history?

Liverpool’s 2005 Istanbul comeback — coming from 3-0 down at half-time to beat AC Milan on penalties — is widely regarded as the single most astonishing result in UCL history. Deportivo La Coruña’s 4-0 win over AC Milan in 2004 (after losing 4-1 in the first leg) and Ajax’s elimination of Real Madrid and Juventus in 2018-19 are close rivals.

Has the UCL ever been won by a true underdog?

Yes — Nottingham Forest (1979, 1980) had only recently been promoted to the English top flight, and Porto (2004) under Mourinho were considered heavy underdogs against AC Milan and Monaco. Steaua Bucharest (1986) defeating Barcelona remains the most unlikely UCL/European Cup winner in history.

What was the Miracle of Istanbul?

The 2005 UCL Final between Liverpool and AC Milan — Liverpool trailed 3-0 at half-time but scored three goals in six minutes early in the second half through Gerrard, Smicer, and Xabi Alonso (penalty). The match ended 3-3 after extra time, with Liverpool winning on penalties.

Which club has the most dramatic UCL comeback record?

Real Madrid are widely considered the kings of UCL comebacks — particularly their 2022 run which included multiple late winners and a miraculous comeback against Manchester City. Liverpool also have extraordinary comeback credentials from 2005 and the 2019 comeback against Barcelona.

Has a team ever won the UCL after losing the first leg of the final?

The UCL Final is a single match at a neutral venue (not two legs), so there is no “first leg” of the final. However, clubs have won the UCL after losing the first leg of earlier rounds — Liverpool’s 2005 comeback was from within the same final match rather than across two legs.

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More Football Trivia

• Champions League All-Time Records — 50 Facts That Will Blow Your Mind
• Real Madrid Champions League Trivia — 15 Titles and Counting
• Champions League 2025-26 Season Quiz

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