Skip to main content
🎉 Join The Club
- Join our community
17
Member Features
24/7
Access Available
5K+
Active Members
🎯
Live Q&A Sessions
Weekly interactive sessions
🏆
Member Competitions
Win exclusive prizes
📚
Exclusive Content
Premium articles & videos
⚡
Early Access
First to see new features
💬
Private Forums
Connect with members
🎁
Monthly Rewards
Surprise gifts & perks
GET CLUB ACCESS QUICK
For the quickest way to join, simply enter your email below and get access. We will send a confirmation and sign you up to our newsletter to keep you updated on all your football news.
By submitting your information, you confirm you are aged 16 or over, have read our Privacy Policy and agree to the Terms & Conditions . Geographical rules apply.
FIND OUT ABOUT OUR MAGAZINE
Want to subscribe to the magazine? Click the button below to find out more information.
Find out more

Get Club Access Quick

Join The Club for quick access. Enter your email below and we'll send confirmation plus sign you up to our newsletter.

By submitting your information, you confirm you are aged 16 or over, have read our Privacy Policy and agree to the Terms & Conditions. Geographical rules apply.

FourFourTwo FourFourTwo FOOTBALL NEWS, FEATURES, QUIZZES
UK EditionUK AU EditionAustralia US EditionUS CA EditionCanada KR Edition대한민국 TR EditionTürkiye
Sign in
  • View Profile
  • Sign out
  • Soccer Cleat Buying Guides
  • Newsletter
  • News
  • Video
  • Features
  • Quizzes
  • Clubs
  • Membership
  • More
    • Interviews
    • The Magazine Archive
    • Subscribe
    • Lists
    • How to Watch
    • About
FourFourTwo Magazine
FourFourTwo Magazine
Why subscribe?
  • Fascinating feature articles, covering everything from grass-roots football to the international scene
  • 'ACCESS ALL AREAS' pass to exclusive interviews with the biggest and best names in the game!
From$29.99
Subscribe now
Don't miss these
Real Madrid's Brazilian forward Vinicius Junior kisses his jersey's badge to celebrate Valladolid's own goal during the Spanish league football match between Real Madrid CF and Real Valladolid FC at the Santiago Bernabeu stadium in Madrid on November 3, 2018.
Quiz Quiz! Can you guess 100 correct answers in FourFourTwo's Big Badge Quiz?
Kevin De Bruyne applauds the Manchester City fans after his final game for the club, against Fulham, in May 2025.
Quiz Quiz! Can you sort these players, clubs and more from earliest to latest?
Spot the Ball
Quiz Quiz! Can you spot the ball in these 10 memorable Premier League moments?
Quickfire Quiz
Quiz Quickfire Quiz 2: Can you answer 10 questions in 90 seconds?
Football facts
Lists 200 niche, surprising and mind-blowing football facts to help you ace pub quizzes
Can you name Europe's most successful teams?
Competition & Tournament Quizzes Quiz! Can you name the 10 most successful clubs from each of Europe's top five leagues?
Sports facilities of Football Club Barcelona. Camp Nou
Quiz Quiz! Can you name the cities with the 20 biggest football stadiums in the world?
FourFourTwo's Dating Game
Quiz FourFourTwo's Dating Game, 28/11/25: Celtic's Lisbon Lions
Nick Frost
Quiz Quiz! Can you tell us which movies and TV shows these 20 football shirts are from?
Champions League logo on the pitch during the UEFA Champions League semi-final first leg match between AC Milan and FC Internazionale at San Siro on May 10, 2023 in Milan, Italy.
Team Quizzes Quiz! Can you name the top 50 clubs in the all-time Champions League table?
FourFourTwo's Champions League Predictor
Competition FourFourTwo's Champions League Predictor: Tell us the results of every UCL fixture and win a subscription to FourFourTwo magazine
Manuel Neuer of Bayern Muenchen controls the ball during the UEFA Champions League 2024/25 League Phase MD1 match between FC Bayern München and GNK Dinamo at Allianz Arena on September 17, 2024 in Munich, Germany.
Quiz Quiz! Can you name Bayern Munich's top 25 appearance makers in the Champions League?
Ranked! Every Premier League kit from worst to best
Lists Ranked! Every Premier League kit from worst to best
MADRID, SPAIN - JANUARY 22: A general view of the inside of the stadium prior to the UEFA Champions League 2024/25 League Phase MD7 match between Real Madrid C.F. and FC Salzburg at Estadio Santiago Bernabeu on January 22, 2025 in Madrid, Spain. (Photo by Aitor Alcalde - UEFA/UEFA via Getty Images)
Quiz Quiz! Can you name every stadium in the Champions League this season?
Ronaldo, Ronaldinho, Rivaldo and Kaka
Player Quizzes Quiz! Can you name the club these players ALL played for?
Trending
  • Transfers
  • Interviews
  • Messi
  • Ronaldo
  • EPL
  • WATCH the EPL
  1. Competition

15 Champions League shocks that shook the world

Features
By Alasdair Mackenzie published 18 September 2018

Nobody saw these shock Champions League results coming...

When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

Beware the banana skins

Beware the banana skins

With another season of Champions League football upon us, Europe’s premier club competition appears to be more dominated than ever by cash fuelled mega-clubs.

However, winning the thing has rarely proven easy – even for the continent’s biggest and most illustrious sides. As the following examples demonstrate, domestic dominance and European pedigree can count for nothing if you’re not careful…

Page 1 of 16
Page 1 of 16
Brondby 2-1 Bayern Munich, 1998/99

Brondby 2-1 Bayern Munich, 1998/99

There was a wonderful symmetry about Bayern’s Champions League heartache of 1998/99.

While Ole Gunnar Solskjaer’s last-minute final winner for Manchester United still sets pulses racing in Salford and beyond all these years later, in Denmark it’s the memory of a comparably impressive comeback that burns brightest.

The game looked to be gone for Brondby when Markus Babbel struck with 15 minutes remaining, but strikes in the 88th and 89th minutes for the Danes (the second a stunning individual effort from Allan Rvan) floored the German giants and dealt Alex Ferguson a handy blueprint for later in the season.

Page 2 of 16
Page 2 of 16
Celtic 2-1 Barcelona, 2012/13

Celtic 2-1 Barcelona, 2012/13

They say there is nothing quite like Celtic Park on a Champions League night, but this performance produced the mother of all atmospheres as Neil Lennon’s side sent Lionel Messi & Co. packing.

Tony Watt’s now-legendary goal, which put the Bhoys 2-0 up, came between Victor Wanyama’s opener and a consolation from Barcelona’s Argentine wizard. The Spaniards went into the game having won the competition twice in the last four years, and with the likes of Messi, Xavi, Andres Iniesta and Alexis Sanchez in their line-up.

The result, achieved with only 16.4% possession, helped the Scots reach the last 16 – the last time they made it to the knockout stage – but their run was ended emphatically there by Juventus in a 5-0 aggregate defeat.

Page 3 of 16
Page 3 of 16
Deportivo 4-0 Milan, 2003/04

Deportivo 4-0 Milan, 2003/04

Everything is context as far as Milan’s limp collapse to Deportivo La Coruna in the 2004 quarter-finals is concerned.

The Serie A giants had dominated in a 4-1 first-leg victory in Italy and travelled to Galicia safe in the knowledge that no team had ever overturned a three-goal aggregate deficit in the Champions League.

Amid such hubris, however, are European dreams turned to ashes: the Rossoneri were pelted 4-0 at La Riazor (having hammered the same opposition by the same score on the same pitch the previous season) and skulked home wondering what had hit them.

Page 4 of 16
Page 4 of 16
Barcelona 0-4 Dynamo Kiev, 1997/98

Barcelona 0-4 Dynamo Kiev, 1997/98

When Barcelona were pitted against Dynamo Kiev for the 1997 group stage, the continent sat upright and took notice. Ukrainian legend Valeriy Lobanovskiy had built a Dynamo side that could not only match the great Soviet teams that had swept up a record 13 league titles in the former USSR, but that was considered a contender for the European Cup itself.

When Kiev beat Barça 3-0 at the Olympic Stadium in October, an upset at the Camp Nou didn’t seem so unlikely – but even in their worst nightmares, Louis van Gaal’s team wouldn’t have expected the hammering that was to follow.

Shevchenko hit a first half hat-trick as Lobanovskiy watched his side canter to a 4-0 win.

Page 5 of 16
Page 5 of 16
Monaco 3-1 Real Madrid, 2004/05

Monaco 3-1 Real Madrid, 2004/05

For Real Madrid, defeats haven’t come much more devastating than the quarter-final exit to Monaco in 2005, which derailed them from what appeared to be a simple path to La Decima.

The Merengues led 5-2 just before half-time in the second leg before Monaco launched the unlikeliest of assaults, helped by former Real favourite Fernando Morientes – on loan in the principality from Madrid. Ludovic Giuly bagged one of his two goals before the break and added another after Morientes had fired in against his old club just after the interval.

Monaco's two away goals in the 4-2 first-leg defeat made the difference in the 5-5 aggregate score, ensuring a memorable night at the Stade Louis II as the French outfit dumped out the competition's most successful side.

Page 6 of 16
Page 6 of 16
Chelsea 1-1 Rosenborg 2007/08

Chelsea 1-1 Rosenborg 2007/08

Remembered not so much for the result as the storm that came after Chelsea's timid draw with unfancied Rosenborg in London proved to be the final straw in Jose Mourinho’s increasingly strained relationship with Roman Abramovich.

Just 25,000 fans headed to Stamford Bridge for Jose’s ignominious swansong before the Russian billionaire embarked on a trigger-happy seven years of managerial chaos.

The Blues still comfortably got through their Champions League group, before beating Olympiakos, Fenerbahce and Liverpool to tee up a Moscow final against Manchester United. Cue rain, and that slip.

Page 7 of 16
Page 7 of 16
Lazio 0-1 Leeds, 2000/01

Lazio 0-1 Leeds, 2000/01

Memories of Champions League glory may now seem distant for the Elland Road faithful, but those old enough to remember will reflect fondly on the night they upset the Italian champions on their own turf.

After an opening day defeat in the second group stage to Real Madrid, Alan Smith’s goal was enough to give the Yorkshire side a superb win against one of the European giants of the time; a side featuring the likes of Alessandro Nesta, Juan Sebastian Veron and Hernan Crespo.

The deserved win for Leeds set them on a course to the last four, with back-to-back wins over Anderlecht and a thrilling final day 3-3 draw with the Roman club enough to book them a semi against Valencia.

Page 8 of 16
Page 8 of 16
Lille 1-0 Man United, 2005/06

Lille 1-0 Man United, 2005/06

The knock-on effect of Manchester United’s shock 1-0 loss at the Stade de France to outsiders Lille in 2005 wasn’t fully appreciated until the final group standings, when the Old Trafford side sat rock bottom and were confronted with a humiliating early exit.

Incredibly it was the only goal Lille scored in six group games, yet they still managed to finish ahead of United and parachute into the UEFA Cup. If it’s not your year...

Page 9 of 16
Page 9 of 16
Real Mallorca 1-0 Arsenal, 2001/02

Real Mallorca 1-0 Arsenal, 2001/02

Arsenal have been no strangers to opening-day European pain. In 2001 it was Champions League debutants Real Mallorca who handed the Gunners the worst possible start, after Ashley Cole’s clumsy tackle on Albert Luque led to a red card, penalty and mountain to climb.

Things got worse for Arsene Wenger when his side lost to Panathinaikos in Greece a month later, and they needed a 3-1 victory over the Spaniards at Highbury in December to sneak through from a less-than-arduous first group stage. They didn't make it past the second, though, bowing out with Juventus behind Bayer Leverkusen and Deportivo.

Page 10 of 16
Page 10 of 16
Dynamo Kiev 2-0 Real Madrid, 1998/99

Dynamo Kiev 2-0 Real Madrid, 1998/99

Save for a remarkable change in fortunes, 1998/99 was the closest Kiev are ever likely to get to lifting European football’s biggest prize.

On their superb run to the semi-finals they collected a handful of worthy scalps, but the manner in which they dispatched the holders in the quarter-final showed Valeriy Lobanovskiy’s tactical genius at its best.

Andriy Shevchenko again was the deadly finisher on hand to crush Real Madrid, but this was a team whose gears turned seamlessly throughout.

Page 11 of 16
Page 11 of 16
Newcastle 3-2 Barcelona, 1997/98

Newcastle 3-2 Barcelona, 1997/98

In 1997, the Champions League broke with four decades of tradition and ceased to be exclusively reserved for champions.

Eight league runners-up from the continent’s strongest leagues were admitted to pit themselves against Europe’s best, and the ‘Champions’ League became a nominal homage to a simpler time. History will record Newcastle United as the first non-champions ever to score in the competition in September 1997.

However, far more remarkable was the Faustino Asprilla hat-trick inside 49 minutes that set the Magpies on course for a famous and surprising victory against heavyweights Barcelona. Late goals from Luis Enrique and Luis Figo weren't enough to deny Newcastle their famous win. 

Page 12 of 16
Page 12 of 16
Sturm Graz, 2000/01

Sturm Graz, 2000/01

Sturm Graz’s story wasn’t so much one of a shock result, but a sequence of surprising outcomes that made it a memorable campaign. Things couldn’t have started worse as Rangers handed out a 5-0 thrashing at Ibrox on day one, and by the halfway point they had suffered another 5-0 reverse, this time to Monaco.

Remarkably the Austrians went on not only to progress to the next round but to top their group – with both Rangers and Monaco failing to make it through. Home wins against the Scottish and French sides were added to a win and a draw against Galatasaray.

They finished third in the second group stage with – guess what? – a 5-0 defeat coming along the way, this time at the hands of Valencia.

Page 13 of 16
Page 13 of 16
Anderlecht 2-1 Manchester United, 2000/01

Anderlecht 2-1 Manchester United, 2000/01

United were run ragged at times by the attack-minded Belgians, with Canadian striker Tomasz Radzinski’s first-half brace giving them a handsome lead that the Premier League side couldn’t fight back from, despite Denis Irwin’s penalty.

It was a big upset for Alex Ferguson’s star-studded side, who had been crowned champions of Europe as recently as 1999 and were up against an Anderlecht team making its first appearance in the Champions League for five years. What made the result even more surprising was that it came just over a month after the Red Devils had handed them a comprehensive 5-1 thrashing at Old Trafford.

Regardless, the Belgians topped the group before suffering elimination in the second group stage.

Page 14 of 16
Page 14 of 16
APOEL 1-0 Lyon (4-3 pens), 2011/12

APOEL 1-0 Lyon (4-3 pens), 2011/12

"I think we haven’t realised what we’ve achieved yet." Those were the words of APOEL vice-president Theo Kyriakides after the Cypriot club’s extraordinary last 16 victory over Lyon on penalties.

Beginning their journey with a mid-July trip to Albania in the second qualifying round, the Nicosia outfit fought through three rounds of qualifiers before remarkably topping their group ahead of Zenit, Porto and Shakhtar Donetsk.

With a budget of just €9m and crowds rarely breaking 10,000, it was no wonder that their shootout victory over the French giants prompted celebrations long into the night. The victory earned them a glamour quarter-final tie against Real Madrid, who were ruthless in an 8-2 aggregate triumph.

Page 15 of 16
Page 15 of 16
Inter 1-5 Arsenal, 2003/04

Inter 1-5 Arsenal, 2003/04

The autumn of 2003 was a puzzler for Arsene Wenger. His team were brushing all aside in England at the start of a remarkable 49-match unbeaten run, but their European opponents weren't proving so forgiving. 

Inter came to London and strolled to a 3-0 victory, Lokomotiv Moscow held the Gunners to a goalless draw, then Dynamo Kiev took advantage of some Jens Lehmann hijinks near the centre circle to grab a 2-1 win and leave Wenger's men bottom.

When Ashley Cole scored a late winner against Kiev at Highbury, however, Arsenal were sparked into life. Five goals on a must-win night at San Siro in November brought Europe to a standstill – and the Gunners to the last 16.

Page 16 of 16
Page 16 of 16
TOPICS
Premier League Champions League
Alasdair Mackenzie

Alasdair Mackenzie is a freelance journalist based in Rome, and a FourFourTwo contributor since 2015. When not pulling on the FFT shirt, he can be found at Reuters, The Times and the i. An Italophile since growing up on a diet of Football Italia on Channel 4, he now counts himself among thousands of fans sharing a passion for Ross County and Lazio. 

Read more
The Champions League trophy in Trafalgar Square, London ahead of the 2024 final at Wembley
Quiz! Can you guess 50 correct answers in FFT's Big Champions League Quiz?
 
 
Champions League logo on the pitch during the UEFA Champions League semi-final first leg match between AC Milan and FC Internazionale at San Siro on May 10, 2023 in Milan, Italy.
Quiz! Can you name the top 50 clubs in the all-time Champions League table?
 
 
Cristiano Ronaldo celebrates after scoring for Real Madrid against Marseille in the Champions League in September 2009.
Quiz! Can you name every club to qualify for the Champions League from Europe's top five leagues?
 
 
Cristiano Ronaldo celebrates after scoring for Real Madrid against Bayern Munich in April 2017.
Quiz! Can you name the top 20 Champions League scorers by their clubs?
 
 
Fireworks light up the London skyline over the Spotify Camp Nou during the farewell after the last match at the stadium ahead of the remodelling works at the end of the LaLiga Santander match between FC Barcelona and RCD Mallorca at Spotify Camp Nou on May 28, 2023 in Barcelona, Spain.
Quiz! Can you name every city to have hosted a Champions League game?
 
 
Milos Kerkez of Liverpool looks dejected following defeat in the Premier League match between Crystal Palace and Liverpool at Selhurst Park on September 27, 2025 in London, England.
Quiz! Can you name the last 100 clubs to defeat the Premier League champions?
 
 
Latest in Competition
World Cup 2026 squads: The FIFA World Cup Trophy is seen during the Commercial Partners Summit at Marriott Georgetown Hotel on December 03, 2025 in Washington, DC.
World Cup 2026 squads: Every nation's latest selection
 
 
LUTON, ENGLAND - OCTOBER 31: The Emirates FA Cup trophy gets a polish before the Emirates FA Cup First Round match between Luton Town and Forest Green Rovers on October 31, 2025 in Luton, England. (Photo by Eddie Keogh/Getty Images)
When is the FA Cup third-round draw? Date, time, teams and ball numbers
 
 
A Newcastle United fan wearing a Father Christmas outfit in the stands
Why is there only one Premier League game on Boxing Day this year?
 
 
MANCHESTER, ENGLAND - OCTOBER 04: Ruben Amorim, Manager of Manchester United, reacts during the Premier League match between Manchester United and Sunderland at Old Trafford on October 04, 2025 in Manchester, England. (Photo by Gareth Copley/Getty Images)
Manchester United's bizarre Bruno Fernandes glitch stands between festive banana skin and European return
 
 
Channel 4 showing EVERY Africa Cup of Nations game with exclusive rights package in UK and Ireland
 
 
2026 FIFA World Cup trophy ahead of the 2026 FIFA World Cup and European Play-Off draw and Play-Off Tournament draw at the FIFA's Home of Football in Zurich on November 20, 2025.
Who is performing at the 2026 FIFA World Cup group stage draw?
 
 
Latest in Features
Argentina World Cup 2026 squad: Argentina forward Lionel Messi has cast doubt over his participation at the 2026 World Cup
Argentina World Cup 2026 squad: Lionel Scaloni's latest selection ahead of the World Cup draw
 
 
LONDON, ENGLAND - DECEMBER 3: during the Premier League match between Arsenal and Brentford at Emirates Stadium on December 3, 2025 in London, England. (Photo by Marc Atkins/Getty Images)
Is Arsenal's Declan Rice injured this weekend? Early Premier League injury news
 
 
Austria World Cup 2026 squad: Austria players celebrate in front of the fans after qualifying for the 2026 World Cup after victory in the FIFA World Cup 2026 qualifier match between Austria and Bosnia and Herzegovina at on November 18, 2025 in Vienna, Austria.
Austria World Cup 2026 squad: Ralf Rangnick's latest selection ahead of the World Cup draw
 
 
Haiti World Cup 2026 squad: Haiti's players pose for a team photo ahead of the 2026 FIFA World Cup Concacaf qualifier football match between Costa Rica and Haiti at the National Stadium in San Jose on September 9, 2025.
Haiti World Cup 2026 squad: Sebastien Migne's latest selection ahead of the World Cup draw
 
 
Curacao World Cup 2026 squad: Curacao's players pose for a team photo before the start of the World Cup qualifier football match between Jamaica and Curacao at the National Stadium in Kingston, Jamaica on November 18, 2025.
Curacao World Cup 2026 squad: Dick Advocaat's latest selection ahead of the World Cup draw
 
 
Panama World Cup 2026 squad: Panama's forward #18 Cecilio Waterman (L) celebrates with teammate defender #15 Eric Davis after scoring his team's second goal during the 2026 FIFA World Cup Concacaf qualifier football match between Guatemala and Panama at the Manuel Felipe Carrera stadium in Guatemala City on November 13, 2025.
Panama World Cup 2026 squad: Thomas Christiansen's latest selection ahead of the World Cup draw
 
 
LATEST ARTICLES
  1. Argentina World Cup 2026 squad: Argentina forward Lionel Messi has cast doubt over his participation at the 2026 World Cup
    1
    Argentina World Cup 2026 squad: Lionel Scaloni's latest selection ahead of the World Cup draw
  2. 2
    World Cup 2026 squads: Every nation's latest selection
  3. 3
    Is Chelsea's Cole Palmer injured this weekend? Early Premier League injury news
  4. 4
    Is Man United vs West Ham on TV? Live streams, preview, how to watch the midweek Premier League clash
  5. 5
    When is the FA Cup third-round draw? Date, time, teams and ball numbers

FourFourTwo is part of Future US Inc, an international media group and leading digital publisher. Visit our corporate site.

Add as a preferred source on Google
  • Terms and conditions
  • Contact Future's experts
  • Privacy policy
  • Cookies policy
  • Accessibility statement
  • Careers
  • About FourFourTwo
  • Advertise with us
  • Worldwide
  • How to pitch to FourFourTwo

© Future US, Inc. Full 7th Floor, 130 West 42nd Street, New York, NY 10036.

Please login or signup to comment

Please wait...