Ranked! The 10 most difficult Champions League Groups of Death EVER

The 10 most difficult Champions League Groups of Death EVER: Gareth Bale of Spurs takes on Lucio of Inter Milan during the UEFA Champions League Group A match between Tottenham Hotspur and Inter Milan at White Hart Lane on November 2, 2010 in London, England.
Gareth Bale of Spurs takes on Lucio of Inter Milan during the UEFA Champions League Group match between Tottenham Hotspur and Inter Milan (Image credit: Clive Rose/Getty Images)

The Champions League group stage isn't the fun part, according to some. It's a pre-amble to the exciting two-legged ties that come after Christmas, where the real competition begins. The part where we're rid of the Croatian league champions and Sevilla have inevitably dropped to the Europa League.

Well… rubbish. That's what we say to that. The group stages of the Champions League are just a part of the competition, whether we're being introduced to a young Erling Haaland, witnessing more Messi madness or just enjoying two giants of the continent going hammer and tongs for one another, safe in the knowledge that they'll probably beat Club Brugge and still get through regardless. 

But sometimes, there is no Brugge to fall back on (sorry, guys). Sometimes, all four clubs in a group are in with a shout of qualification. Now, this is what the Champions League is all about – and in this list, we're not counting the short-lived second group stage, of course…

10. 1998/99, Group B: Juventus, Galatasaray, Rosenborg, Athletic Bilbao

Ismael Urzaia of Athletic Bilboa takes on Alessandro Birindelli of Juventus during the UEFA Champions League match at the San Mames Stadium in Bilboa, Spain.

Alessandro Birindelli of Juventus tussling with Ismael Urzaia of Athletic Bilbao. (Image credit: Mike Hewitt /Allsport)

Draw five out of six games in your first round and you're probably not seeing the second, right? Not Juventus, who actually topped Group B in one of the most competitive four-team slogs that the Champions League had ever witnessed in 1998. 

Look at these sides on paper now and the Old Lady are probably batting all three competitors away with ease – but not so in 1998. Rosenborg were Champions League regulars at this point and could mix it with the big boys, while Galatasaray boasted the likes of Hakan Sukur and Umit Davala, and would go on to win the UEFA Cup in 2000. Both were domestic champions – and both garnered a whopping eight points a-piece in the group, finishing behind Juve on goal difference.

Even Athletic Bilbao were strong back then and had finished second in La Liga ahead of Real Madrid. They collected six points that season: two fewer than the Italian leaders and with just as many wins under their belt. Juventus would march onto the semi-finals, too. 

9. 2003/04, Group B: Arsenal, Lokomotiv Moscow, Inter Milan, Dynamo Kyiv

Arsenal FC vs FC Internazionale. Thierry Henry (Arsenal) and Cristiano Zanetti (Inter). Football, Ligue des Champions 2003-2004. Arsenal contre Inter de Milan. Thierry Henry (Arsenal) et Cristiano Zanetti (Inter).

Arsenal's Thierry Henry trying to beat Inter Milan's Cristiano Zanetti for pace. (Image credit: Olivier Prevosto/Photo & Co./Corbis/VCG via Getty Images)

Kids today just won't believe you if you tell them that Lokomotiv Moscow and Dynamo Kyiv were difficult places to go in the Champions League – let alone that Arsenal and Inter Milan were two of the best sides in the competition.

The side soon to become the Invincibles looked dead and out of the competition three matches into the group stage before a miraculous recovery. This was the season that they smacked Inter for five – who in turn had sausaged them 3-0 at Highbury – while Lokomotiv and Dynamo were well-organised teams that westerly clubs didn't particularly like visiting.

In a strange old season for the Champions League, Chelsea, Porto, Deportivo and Monaco all made the semi-finals. Arsenal's struggles early on were just foreshadowing for how tough the competition was this year. 

8. 2021/22, Group B: Liverpool, Atletico Madrid, Porto, AC Milan

Mohamed Salah of Liverpool scores their side's third goal from the penalty spot during the UEFA Champions League group B match between Atletico Madrid and Liverpool FC at Wanda Metropolitano on October 19, 2021 in Madrid, Spain.

Mohamed Salah of Liverpool scores their side's third goal from the penalty spot against Atletico Madrid at Wanda Metropolitano. (Image credit: Angel Martinez/Getty Images)

Ultimately, this group was made to look incredibly easy by a Liverpool squad who stormed to a maximum 18 points without breaking a sweat. Looking at the quality of the four teams, it was a brilliant achievement. 

The Merseysiders were among the favourites for the competition and came within a whisker of the Quadruple that season. Atletico Madrid were knockout regulars, with added Antoine Griezmann and fresh from winning the title. The Porto side in question had made the quarters last time, knocking out Cristiano Ronaldo and Juventus – before the Reds themselves nicked Luis Diaz – while AC Milan were en route to a Serie A title. 

Had the draw have been different, any of these sides could've topped a group of their own. Liverpool's greatest feat in that group was making everyone else look ordinary. 

7. 2010/11, Group A: Tottenham Hotspur, Inter Milan, Twente, Werder Bremen

FC Twente Enschede-player Bryan Ruiz (R) fights for the ball with Esteban Cambiasso of Inter Milan during their Champions League group A football match in Enschede, on September 14, 2010. AFP PHOTO / ANP /VINCENT JANNINK netherlands out - belgium out.

Twente star Bryan Ruiz fights for the ball with Esteban Cambiasso of Inter Milan. (Image credit: VINCENT JANNINK/AFP via Getty Images)

Yep, this was the season that Gareth Bale did that

European champions Inter Milan were the headliners of the group, with Tottenham announcing themselves with Bale, Luka Modric and co. in tow. Twente were weirdly strong, too, with Bryan Ruiz pulling strings for Luuk de Jong and Nacer Chadli (remember him, Spurs fans?). The Dutch side finished third with a wholly respectable six points. 

Then there was Werder Bremen, who brought up the rear but boasted Claudio Pizarro, Torsten Frings and Per Mertesacker alongside youngsters Mesut Ozil and Marko Arnautovic. Each side pulled off their own shock that season – and each were wonderfully entertaining to watch. 

6. 2002/03, Group A: Arsenal, Borussia Dortmund, Auxerre, PSV

Tomas Rosicky of Dortmund and Benjani of Auxerre during The Champions League group A match between BV Borussia Dortmund and AJ Auxerre at The Westfalen Stadium in Dortmund, Germany on September 25, 2002.

Tomas Rosicky of Dortmund and Benjani of Auxerre during the Champions League group match Borussia Dortmund and Auxerre. (Image credit: Stuart Franklin/Getty Images)

2002's Group A is a cult hero special. Seriously, just look at the names for each side.

Borussia Dortmund, managed by Matthias Sammer, had Tomas Rosicky, Lars Ricken, Sunday Oliseh and Jan Koller in their side. Auxerre, led by the legendary Guy Roux, had Djibril Cisse, Philippe Mexes and Khalilou Fadiga. PSV were managed by Guus Hiddink, with Mateja Kezman and Jan Vennegoor of Hesselink up front ahead of Park Ji-Sung, Arjen Robben and Mark van Bommel. 

Four points separated top (Arsenal) from bottom (PSV) – and both sides lost the same number of games. The streets would certainly never forget this group in a hurry. 

5. 1994/95, Group A: Goteborg, Barcelona, Manchester United, Galatasaray


Manchester United full-back Denis Irwin leads his team off the Camp Nou turf following defeat to Barcelona.  (Image credit: David Rogers/ALLSPORT)

Most Swedish triumphs in recent history either involve Zlatan Ibrahimovic or the Eurovision Song Contest. In 1994, however, Goteborg etched their names in Scandinavian archives by topping this hellishly difficult group.

That's right: Johan Cruyff and Alex Ferguson were slogging it out between each other for second, as the bulk of Sweden's golden generation – the Swedes finished third at the World Cup that summer – cruised through the first stage of the Champions League with all the ease of a flatpack-assembly cabinet. 

Let's not forget either that Galatasaray, featuring future Blackburn Rovers trio Hakan Unsal, Hakan Sukur and Tugay, had been dominant in their native Turkey, too, turning over Barcelona in Istanbul that season. This was back in the days when only champions would make the competition – making this a group of serious pedigree as well as incredible talent.

4. 2002/03, Group E: Juventus, Newcastle United, Dynamo Kyiv, Feyenoord

Newcastle's Laurent Robert (C) takes the ball past Juventus' Pavel Nedved (R) while Lilian Thuram (L) runs back during the Champions League Group E match at St. James's Park in Newcastle 23 October 2002.

Newcastle's Laurent Robert takes the ball past Juventus' Pavel Nedved at St. James's Park. (Image credit: ADRIAN DENNIS/AFP via Getty Images)

Newcastle didn't just used to be good pre-Mike Ashley – they were absolutely electric. OK, so they got walloped in their opening three games but having the likes of Alan Shearer, Laurent Robert, Nobby Solano and Gary Speed meant they weren't down for long.

The Toon qualified via beating Juventus – eventual runners-up in the competition with Ballon d'Or-winning Pavel Nedved, David Trezeguet, Alessandro Del Piero and Edgar Davids among others – along with UEFA Cup holders Feyenoord and Diogo Rincon-aided Dynamo Kyiv, who were horribly awkward to play against. Newcastle were the first side to qualify from a group after losing their first three games, proving how tough that pool really was. 

“Eventually we just reset and said, 'You know what - let’s just play the way we want to play',” Jermaine Jenas told FFT. “Once we got teams back to St. James’s Park and we had that big win against Juve, it was just meant to be.”

3. 2020/21, Group B: Real Madrid, Borussia Monchengladbach, Shakhtar Donetsk, Inter Milan

Head Coach of FC Internazionale Antonio Conte shakes hands with the head coach of Real Madrid Zinédine Zidane before the UEFA Champions League Group B stage match between FC Internazionale and Real Madrid at Stadio Giuseppe Meazza on November 25, 2020 in Milan, Italy.

Former Juventus teammates Antonio Conte and Zinedine Zidane embrace before their respective clubs – Inter Milan and Real Madrid – do battle in the Champions League. (Image credit: Claudio Villa - Inter/Inter via Getty Images)

You know a group's strong if Antonio Conte is finishing bottom. This was the season that Romelu Lukaku would fire Inter Milan to a first title in a decade and earn a £100 million move back to Chelsea… and they were still the weakest side in the group.

Real Madrid, naturally, topped it – and even they were rattled. Marco Rose's free-scoring Borussia Monchengladbach played some of the most high-intensity football in that season's Champions League, Marcus Thuram and Alessane Plea scoring for fun in routs of Shakthar – who were none too shabby either, having been knocked out of the Europa League semi-finals the summer previous. 

Ultimately, none of the four sides would win the competition – but each of them provided some of the biggest thrills. 

2. 2018/19, Group B: Barcelona, Tottenham Hotspur, Inter Milan, PSV

Barcelona's Argentinian striker Lionel Messi (L) scores his team's fourth, and his second goal past Tottenham Hotspur's French goalkeeper Hugo Lloris during the Champions League group B football match match between Tottenham Hotspur and Barcelona at Wembley Stadium in London, on October 3, 2018.

Barcelona's Lionel Messi scores his team's fourth, and his second goal past Tottenham Hotspur's Hugo Lloris at Wembley Stadium. (Image credit: ADRIAN DENNIS/AFP via Getty Images)

A Champions League group doesn't have to include Inter Milan in it to be considered strong but it certainly helps. This one – also managed by Conte – bombed out early and finished silver in the Europa League. 

Barcelona were magnificent that season in the league, while Lionel Messi singlehandedly cut through Tottenham in north London like a hot knife. Barça would have reached the Champions League final, too, but for an Anfield miracle and a quickly taken corner, while PSV that season had future Spurs star Steven Bergwijn and Hirving Lozano on the flanks and Luuk de Jong up front.

And there were Spurs themselves, who earned a magnificent Camp Nou point and made it all the way to Madrid before falling to Liverpool. Group B that season prepared them for a rollercoaster knockout stage of coming back from the brink. 

1. 2012/13, Group D: Borussia Dortmund, Real Madrid, Ajax, Manchester City

Sergio Aguero of Manchester City competes with Mario Gotze of Borussia Dortmund during the UEFA Champions League Group D match between Manchester City and Borussia Dortmund at the Etihad Stadium on October 3, 2012 in Manchester, England.

Sergio Aguero of Manchester City competes with Mario Gotze of Borussia Dortmund at the Etihad Stadium. (Image credit: Alex Livesey/Getty Images)

The most difficult Champions League group in the history of the competition? Put it this way: an attack including Yaya Toure, Sergio Aguero, David Silva and Edin Dzeko finished bottom. 

Ajax pipped Manchester City into third that season with their young side that included Christian Eriksen, Toby Alderweireld and Daley Blind, narrowly picking up four points at the Sky Blues' expense. City meanwhile competed strongly with Jose Mourinho's Real Madrid, getting a point at home and almost the same away, before succumbing to a late Cristiano Ronaldo winner. 

Jurgen Klopp's Borussia Dortmund were just as strong, topping the table without a loss and going on to meet Los Blancos again in the semi-finals of the competition. We may not a group as fearsome as this for a while – let alone Man City bottom of a group…

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Mark White
Staff Writer

Mark White has been a staff writer on FourFourTwo since joining in January 2020, writing pieces for both online and the magazine. An encyclopedia of football shirts and boots knowledge – both past and present – Mark has also been to the FA Cup and League Cup finals for FFT and has written pieces for the mag ranging on subjects from Bobby Robson's season at Barcelona to Robinho's career. He once saw Tyrone Mings at a petrol station in Bournemouth but felt far too short to ask for a photo.