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  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. 

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