Ranked! 5 Toughest Champions League Groups Ever Ahead of 2023/24 Draw

• The Champions League is here
• The draw of the 2023/24 season will be done on Friday, August 31
• Sports Brief looks at some of the hardest groups in Champions League history

The UEFA Champions League is undoubtedly the best club competition in world football. The best clubs in Europe and the best players in the world battle for the coveted Champions League trophy.

Last season, Manchester City beat Inter Milan in the final to lift their first-ever Champions League trophy, and Pep Guardiola's side are favourites this season again.

Some feel the competition doesn't really start until the Round of 16. They are mistaken because the group stage of the competition offers the most dramatic games and scenarios.

Several top teams have fallen in the group stage, while minnows have achieved the impossible by going past the group stage. Ahead of the 2023/24 group stage draw, Sports Brief looks at the toughest Champions League groups of all time, per Four Four Two.

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Top 5 hardest UCL groups

5. 1994/95, Group A

Teams: Goteborg, Barcelona, Manchester United, Galatasaray

Barcelona and Manchester United are household names in the Champions League, having won the competition multiple times, but in 1994, they were shocked by the Swedish side Goteborg, who topped the group. The Swedish team had most of the country's golden generation, who played a key role as they finished third in the 1994 World Cup in the USA.

Goteborg reached the quarter-final, and even Bayern Munich needed away goals to eliminate them. Barcelona finished second, while the Red Devils finished third.

4. 2002/03, Group E

Teams: Juventus, Newcastle United, Dynamo Kyiv, Feyenoord

Juventus have experienced Champions League heartbreak many times in the last few decades. In the 2002/03 season, they reached the final but lost again. That season, they navigated a tough group that had a solid Newcastle side, Dynamo Kyiv and Feyenoord, who were tough to play against.

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The Magpies lost the opening three games but recovered to qualify. They beat a Juventus team that had Pavel Nedved, David Trezeguet, Alessandro Del Piero and Edgar Davids.

3. 2020/21, Group B

Teams: Real Madrid, Borussia Monchengladbach, Shakhtar Donetsk, Inter Milan

This group was uncomfortable for Inter Milan and Real Madrid. Madrid easily topped the group but had to beat stubborn Monchengladbach and Shakhtar. Shockingly, Inter Milan finished bottom of the group while the German side finished second.

The Ukrainian side beat Real Madrid home and away, but the biggest story was Antonio Conte's Inter finishing bottom.

2. 2018/19, Group B

Teams: Barcelona, Tottenham Hotspur, Inter Milan, PSV

This was one of the most thrilling groups in the last few years. Tottenham were at their best while Barcelona still had Lionel Messi. It was one of the greatest Champions League seasons of all time. It featured a few upsets in the knockout stages, and both Tottenham and Barcelona were involved.

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Barca thought they had wrapped up a final spot but were stunned at Anfield by Liverpool, while Tottenham shocked a brilliant Ajax team to progress to the final.

Conte's Inter Milan finished third.

1. 2012/13, Group D

Teams: Borussia Dortmund, Real Madrid, Ajax, Manchester City

This group consisted of European giants and Manchester City before they became the all-conquering force of today. The English side finished bottom of the group despite having stars like Yaya Toure, Sergio Aguero, David Silva and Edin Dzeko.

Dortmund were at the peak of their powers under Jurgen Klopp. They thrashed Jose Mourinho 4-1 in the semis but fell short in the final, narrowly losing to Bayern Munich, who lifted their first Champions League trophy since 2001. They went on to win another one in 2020.

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According to the projection, United could be drawn against Bayern Munich, seven-time winners AC Milan, and Scottish giants Celtic.

Arsenal, on the other hand, face the prospect of being pooled with Barcelona, Rangers, and Turkish giants Galatasaray.