Croatia
Indonesia
Nigeria
South Africa

Sheriff's victory over Real Madrid one of Champions League's biggest shocks like Man United collapse and famous Celtic and Newcastle wins

talksport.com, 29 September 2021, 15:30
The Champions League has a reputation for being a competition where the biggest, richest clubs always prosper.

That's why we love it when that narrative is turned on its head.

Wednesday night saw one of the biggest upsets in recent memory as Moldovan side Sheriff Tiraspol recorded a shock 2-1 victory over Real Madrid at the Santiago Bernabeu.

After taking the lead and seeing Karim Benzema equalise from the penalty spot, a stunning 89th minute winner from Sebastien Thill sent the visiting fans into raptures and put them at the top of Group D with six points from a possible six.

There's a long way to go in the group stage but Sheriff's achievements got us thinking about the Champions League's biggest upsets from over the years.

Have a look at these and see how many you remember.

Newcastle 3-2 Barcelona, 1997/98

It was the first season in which non-champions were allowed to enter the competition, so Newcastle were really upsetting the apple cart by getting involved.

That feeling was heightened when they secured a shock victory over Barcelona at St James' Park thanks to a 49-minute hat-trick from Faustino Asprilla who ran the Catalan giants ragged.

Luis Enrique and Luis Figo did manage to salvage some late consolation but it was a night in which Europe's biggest clubs knew that they wouldn't always have it their own way anymore.

Dynamo Kiev 2-0 Real Madrid, 1998/99

The Ukrainian side made it all the way to the Champions League semi-finals in 1999 and took some significant scalps along the way.

The biggest had to be a victory over reigning champions Madrid in the quarter-finals in which a fresh-faced Andriy Shevchenko wreaked havoc on the Spanish giants.

It was that summer in which the striker was snapped up by AC Milan and Kiev came to the realisation that this was probably the closest they'd get to Champions League glory.

Deportivo 4-0 Milan, 2003/04

Arguably the biggest upset in our list came in 2004.

Fresh from a 4-1 victory at the San Siro, the Italian giants were confident of progressing to the competition's semi-finals.

However the Spanish side had other ideas as Walter Pandiani, Juan Carlos Valeron, Albert Luque and Gonzalo Fran scored a thumping win to silence the travelling Milan fans at La Riazor.

Inter 1-5 Arsenal, 2003/04

While the Gunners were invincible on the domestic front, the same couldn't be said in the Champions League.

After losing 3-0 at home to Inter and stuttering their way through the group stage Arsene Wenger's side went to the San Siro knowing that a big result and even bigger performance would be needed.

Thankfully Henry (2), Freddie Ljungberg, Robert Pires and Edu were on hand to sweep the Italian side away and secure a spot in the last 16 of the competition.

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

Having entered the competition in the second qualifying round it's safe to say that APOEL had relatively modest ambitions going into the campaign.

After topping a group that included Zenit, Porto and Shakhtar Donetsk the Cypriot side faced Lyon in a tie which had the makings of a walkover for the French side.

APOEL had other ideas and a spirited performance and penalty shootout win set up a glamourous quarter-final tie with Real Madrid.

Celtic 2-1 Barcelona, 2012/13

Celtic Park on a Champions League night is something to behold and on this occasion Barcelona were completely overawed by the occasion.

With Lionel Messi, Xavi, Andres Iniesta and Alexis Sanchez in their line-up the Spanish giants were expected to cause chaos but instead it was the Scottish side who came out on top.

Victor Wanyama and Tony Watt scored the decisive goal and ensured that Messi and co flew back to Barcelona in stunned silence.

Young Boys 2-1 Man United, 2021/22

We don't have to travel too far into the past for this one given that it happened early in September.

Manchester United's trip to Young Boys was tipped as a dead-cert for Ole Gunnar Solskjaer's side to get their group stage up and running with three points, particularly given the recent blockbuster arrival of Cristiano Ronaldo.

But despite taking an early lead it was the Swiss side who capitalised on Aaron Wan-Bissaka's sending off and popped up with a late winner to leave the English giants completely shell-shocked.

Top News

23 December 2024 sportsmole.co.uk Yemen and Saudi Arabia will celebrate Christmas Day by facing each other on matchday two of the Arabian Gulf Cup on Wednesday at Jaber Al-Ahmad International Stadium in Kuwait City. 23 December 2024 sportsmole.co.uk First place in Group B of the Arabian Gulf Cup will be at stake on Wednesday as Bahrain and Iraq celebrate Christmas Day at Jaber Al-Ahmad International Stadium in Kuwait. 23 December 2024 sportsmole.co.uk Manchester United transfer target Randal Kolo Muani is very likely to leave Paris Saint-Germain in the January transfer window, according to reports. 22 December 2024 sportsmole.co.uk Manchester City have reportedly set their sights on West Ham United attacker Mohammed Kudus, with Pep Guardiola keen to strengthen his struggling squad. 22 December 2024 sportsmole.co.uk Manchester United are reportedly set to rival Arsenal for the signature of Juventus striker Dusan Vlahovic in the summer of 2025. 22 December 2024 sportsmole.co.uk The final Premier League gameweek before Christmas appropriately served up some crackers, including a festive feast of goals in North London, where Liverpool ran riot in an exhilarating 6-3 win over Tottenham Hotspur. 22 December 2024 talksport.com Even when the pulse settled a little after this compellingspectacle it was still difficult to know quite where to start todissect this nine-goal thriller. 22 December 2024 talksport.com Ange Postecoglou cut an irritated figure as he claimed he's going to stop answering questions about Tottenham's tactics. 22 December 2024 sportsmole.co.uk Tottenham Hotspur have supposedly expressed an interest in signing Borussia Dortmund attacker Julian Brandt next month. 22 December 2024 sportsmole.co.uk Liverpool's Mohamed Salah refused to give anything away when asked whether he could break Ian Rush's all-time goalscoring record after the Reds' remarkable 6-3 win over Tottenham Hotspur. 22 December 2024 sportsmole.co.uk Liverpool's astonishing 6-3 Premier League win over Tottenham Hotspur on Sunday evening saw a multitude of records and achievements surpassed, as the Reds moved four points clear at the top of the table. 22 December 2024 sportsmole.co.uk Al-Ahli have reportedly emerged as the favourites to sign Marcus Rashford, with the Manchester United attacker widely expected to be on the move during the January transfer window. 22 December 2024 talksport.com Everton have become surprise leaders in one statistic across Europe thanks to their draw at home to Chelsea. 22 December 2024 sportsmole.co.uk Liverpool will spend Christmas Day four points clear at the top of the Premier League table thanks to a breathtaking 6-3 win over Tottenham Hotspur in North London. 22 December 2024 talksport.com Kylian Mbappe struck a landmark effort to put himself firmly among Real Madrid's elite. 22 December 2024 sportsmole.co.uk Chelsea head coach Enzo Maresca has insisted that he is "absolutely happy" with his side's goalless draw at Everton on Sunday. 22 December 2024 talksport.com If you thought Mohamed Salah couldn't set yet another record, think again. 22 December 2024 sportsmole.co.uk For a second time in successive Gulf Cup competitions, The United Arab Emirates and Kuwait will meet in the group stage, with this upcoming game taking place on Tuesday at Jaber Al-Amad International Stadium in Kuwait City. 22 December 2024 sportsmole.co.uk Bayer Leverkusen defender Jeremie Frimpong is supposedly not a 'concrete target' for Liverpool amid speculation over Trent Alexander-Arnold's future. 22 December 2024 sportsmole.co.uk Real Madrid moved into second spot in the La Liga table courtesy of a 4-2 success over Sevilla in Sunday afternoon's contest at Bernabeu, with Los Blancos ending 2024 on a high note. 22 December 2024 sportsmole.co.uk Oman and Qatar will compete in the Gulf Cup for the first time in over a decade on Tuesday at Jaber Al-Ahmad International Stadium, each seeking their first victory in this edition of the tournament. 22 December 2024 sportsmole.co.uk Barcelona have reportedly received offers from three clubs for defender Eric Garcia, but the player is pushing against a move away from Catalonia during the January transfer window. 22 December 2024 sportsmole.co.uk Manchester United have broken two unwanted club Premier League records in their humiliating 3-0 home defeat to Bournemouth. 22 December 2024 sportsmole.co.uk New Wolverhampton Wanderers' boss Vitor Pereira earned three points when his side comfortably beat Ruud van Nistelrooy's Leicester City 3-0 away from home on Sunday afternoon in the Premier League. 22 December 2024 talksport.com Aaron Ramsdale was spotted wearing a modified goalkeeper glove in Southampton's Premier League clash at Fulham. 22 December 2024 sportsmole.co.uk Chelsea squandered the chance to go top of the Premier League table for a couple of hours as Everton held the Blues to a goalless stalemate at Goodison Park. 22 December 2024 sportsmole.co.uk Djed Spence has been named in the Tottenham Hotspur starting XI for their Premier League clash with Liverpool, while Luis Diaz and Cody Gakpo get the nod up front for the visitors. 22 December 2024 talksport.com Manchester United were beaten 3-0 by Bournemouth in a defeat that saw Ruben Amorim's side achieve an unwanted record. 22 December 2024 talksport.com Gary Neville believes that Ruben Amorim will allow Marcus Rashford to leave Manchester United for the sake of 'himself and the club'. 22 December 2024 talksport.com Pep Guardiola isn't immune from the sack at Manchester City having continued their unprecedented and dismal run of form.