Ranking the 10 biggest Champions League upsets of all time | OneFootball

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The Champions League is regarded as one of the most coveted competitions in football, but what are the top 10 UEFA Champions League upsets in the history of the iconic tournament?

To see one of the giants lose to an unknown team can be one of the biggest shocks and propel a team into the headlines, and we've seen it happen more than a handful of times. Some absolute goliaths of world football have taken an unexpected L in the biggest tournament in club football, including Real Madrid, Barcelona, Manchester United and AC Milan, and we'll be looking at some of those in this article.

RC Lens 2-1 Arsenal (2023/24)

Champions League newcomers, RC Lens were making just their third-ever appearance in the competition, having competed in both the 1997/1998 and 2002/2003 competitions. After a 20-year hiatus, the French side were back in the big time, following on from a brilliant domestic campaign the preceding season. Drawing away to Sevilla in their opening game, it was clear the lads from France weren’t here to just make up the numbers.

Heading into their clash with fellow returnees, Arsenal, even a buoyant Lens, with a home advantage, were considerable underdogs against Mikel Arteta’s imperiously oiled, well-drilled, title-chasing machine. The Gunners pulled no punches by going a goal to the good via a well-taken Gabriel Jesus goal during the early exchanges.

However, despite Lens’ side costing roughly half a billion less than their opposition, a truly sensational goal from Adrien Thomasson saw the hosts draw level, and in the second half, the unthinkable happened, with one of the most underrated signings of the summer, Elye Wahi netting Lens’ second and subsequent winner.

Manchester United 2-3 Galatasaray (2023/24)

The Red Devils are seemingly in an interminable state of crisis. It’s been a decade since Fergie called time on his decorated career at Old Trafford, and since then the club have had to endure an incessant downward spiral, with calamity after calamity and controversy after controversy. Whether it be the unrest between the fanbase and those at the very top, the recent handling of a plethora of scandals, or the perpetual underperformance on the pitch, many a United fan had probably thought their club had already reached the bottom of the barrel. Unfortunately, for those of a red persuasion in Manchester, as of 3rd October 2023, it was about to get worse, with a home defeat to Galatasaray.

The Turkish side hadn’t won a Champions League game in five years, and with just two wins in their last 24 Champions League matches, even an out-of-form, Manchester United were going into their tie at Old Trafford as overwhelming favourites. With United taking an early lead through a Rasmus Hojlund header, initial nerves were almost immediately settled at a tense Theatre of Dreams.

Those moments of comfort didn’t last long when Wilfred Zaha popped up against his old club to equalise for the Istanbul-based side. Despite United clawing themselves back in front, a calamitous challenge saw Casemiro walk and United were reduced to 10 men. Unsurprisingly, the Süper Lig club seized the initiative, scoring two in quick succession to gift Galatasaray a historic win.

Real Madrid may have won the UEFA Champions League in the previous season by beating Liverpool, but their campaign in the 2021/2022 season got off to a rocky start when they came up against an unknown opponent, Sheriff, who was making their UEFA Champions League debut.

The match took place on 28th September 2001 and would see Sheriff cause an unreal upset by taking the tie 2-1. The Moldovans would shock Los Blancos when Sebastien Thill scored a late winner in the 90th minute at the Bernabeu.

It was an unbelievable win for the underdog team, and that's why it ranks fifth on our list of the top 5 UEFA Champions League upsets!

FC Basel 2-1 Manchester United (2011/12)

Coming off a tough 2010/11 UEFA Champions League Final loss to Barcelona at Wembley, the new UCL season seemed to prove a tough one as the Red Devils would shock the world and not even make it through the group stages.

United would lose out in a group that consisted of Benfica, FC Basel and Otelul Galati. The final nail in the coffin was when they travelled to Switzerland in a must-win game against FC Basel.

Xherdan Shaqiri would prove to be the danger man for Basel, contributing to both goals that would finish Manchester United. Phil Jones would get a goal back, but it was too little too late for United.

Manchester United 1-1 Porto (2003/04)

Look away now, United fans. Being a big and highly successful club does have its occasional downsides, and it’s fair to say the Red Devils have not been immune to an upset or two over the years. Characterised by an overcoat-sporting, Jose Mourinho carting off down the Old Trafford touchline in celebration after Porto bagged an injury-time equaliser, this is one of the most unforgettable Champions League upsets ever. A European colossus at the time, United under Fergie were a consistent title-winning side. However, Jose Mourinho with his villainous energy, was only just making his mark on the sport, galvanising the Portuguese side to their first Champions League Final in 16 years.

Barcelona 1-2 Rubin Kazan (2010/11)

This wasn’t any old Barcelona side, this was the Catalonians at the absolute peak of their powers under the mentorship of Pep Guardiola. The year prior, the Spaniards had seen off Manchester United in the Champions League Final, and were comfortably the best side in Europe, having won the treble.

However, just six months later, during a group stage game with minnows, Rubin Kazan, the Camp Nou was left stunned. The Russians, who were playing in their debut Champions League campaign, turned up to the footballing cathedral in Barcelona and carried out their own sporting sacrament, beating Guardiola’s superstars two goals to one in what was a truly mesmerising affair.

Celtic 2-1 Barcelona (2011/12)

Celtic welcomed the reigning European Champions Barcelona to Celtic Park back in the 2011/2012 season. Despite only recording 16% possession, Celtic were able to take three points away from the Catalan giants, with goals coming from Victor Wanayama and Tony Watt.

Lionel Messi did get a goal back for Barcelona, but it was too late as a shocked Neill Lennon and Celtic fans were jubilant in victory after the final whistle. It was a huge win for the Scottish side, and that is why it sits fourth on our list of the top 5 UEFA Champions League upsets!

AS Monaco 3-1 Real Madrid (2003/04)

The 2003/04 season had plenty of surprises as FC Porto lifted the Champions League trophy defeating the likes of Manchester United on the way. However, one of the biggest shocks in this campaign was the game between AS Monaco and Real Madrid.

Los Blancos were positioned as one of the favourites with their team of galacticos, featuring the likes of David Beckham, Luis Figo, Raul, Ronaldo, Zidane and more. In the first leg against Monaco, they defeated the French side 4-2 in the first leg and looked for sure to advance.

What Madrid didn't expect was that in the second leg, one of their loaned-out players would come to haunt them as Spanish forward Fernando Morientes would be pivotal in the shock 3-1 victory which saw Monaco advance to the semi-finals.

Deportivo La Coruna 4-0 AC Milan (2003/04)

The reigning European Champions AC Milan looked dominant in the 03/04 campaign with them picking up a 4-1 first-leg win in Spain against Deportivo and looked sure to advance in the tournament after goals from Kaka, Shevchenko and Pirlo gave them a huge advantage.

However, what the Italian giants didn't expect, was what occurred when they hosted the Spanish side at the San Siro. Deportivo would take a surging 3-0 lead in the first half with goals coming from Pandiani, Valeron and Luque to level up the tie.

The Spanish side would continue to apply the pressure and would find the winner in the 76th-minute courtesy of Fran in what was a miracle moment in Spain, and that's why it lands at number 1 in our top 5 UEFA Champions League upsets!

AC Milan 3-3 Liverpool (2004/05)

Perhaps the strangest entry in the sense that Liverpool are very much on par, if not a bigger club than the Milanese giants. However, in this particular instance, the 2005 Champions League Final was an exception to that rule, with Carlo Ancelotti’s dominant Milan heading into the final in Istanbul as formidable favourites.

With a star-studded side from one to eleven, including an embarrassment of World Cup-winning riches, the 2003 European Champions were entering their showdown with Liverpool in pursuit of the double. This wasn’t only an upset in the conventional sense of Milan expected to win, but also in how the game panned out. 3-0 up at half-time Ancelotti’s side were in cruise control and looked set to claim their 7th European crown.

Of course, every football fan knows what happened next, as Liverpool mounted the comeback of all comebacks, in what was the most inspired second-half performance, arguably, in football history, and certainly the most memorable Champions League Final. Scoring three goals and going on to win on penalties, this was one of the greatest in-game upsets of all time.