These clubs have been eliminated from this stage of the knockout round in the competition most number of times.

The UEFA Champions League (UCL) is the epitome of club competitions in European football. It is tough to win the competition, but even more challenging to maintain their high performance. It is only clubs like Real Madrid, FC Barcelona, and FC Bayern Munich that frequently appear in the final stages. ‘Round of 16’ may be referred to as the first stage of knockouts, but many big clubs have been trapped in this vicious stage more than once.

Let’s take a look at the top 10 clubs that have most losses in the UCL Round of 16 since 1992-93. (stats via Transfermarkt)

10. Borussia Dortmund – 7 losses

Borussia Dortmund is a regular name in the Champions League every season in German football. They lifted the cup once in the 1996/97 season while also have reached the finals in the 2012/13 season last time. The German giants might not look like a star-studded team of the competition but have been a competitor and a sure-shot team to be in knockouts. 

9. Bayer 04 Leverkusen – 8 losses

Another German club in the Champions League is Bayer Leverkusen. Although, they are not regulars in Champions League football because they have been trailed out by new clubs like RB Leipzig. They have never been able to replicate their league performances in the UCL, so they don’t have any titles to boast about.

8. Manchester United – 8 losses

A key reason why Manchester United is on this list is that they have struggled to perform well in the Champions League after Sir Alex Ferguson left. In addition to their poor performance, the English giant has even failed to be regular in the competition. However, they have won the cup thrice and finished runners-up twice. United has a long history with the Champions League and will look to return to its former glory in the future.

7. AC Milan – 8 losses

In the same vein as Manchester United, AC Milan has a long and storied history in the Champions League but has recently struggled. It is impressive how competitive the Champions League is since the Italians are still trapped in the round of 16 despite being the second-most successful team in the competition.

6. FC Bayern – 9 losses

In German football, FC Bayern is the most successful club and a regular customer of UCL knockouts. While Bayern Munich may not have as many titles as Real Madrid, they are always found in the last eight or last four rounds more often than not. However, the round of 16 has proven challenging for them.

5. Juventus – 10 losses

The Champions League is one of the most unlucky competitions for Juventus. Despite many appearances in the final, the Italian giants have only won the competition twice. The last time they won the competition was in 1996, and since then they have been unable to succeed. The Champions League has seen them tumble 10 times in the round of 16 stages.

4. Chelsea – 10 losses

This season, Chelsea is on the verge of being eliminated by Borussia Dortmund after losing 1-0 at home. This is enough to make it clear why the blues are ranked so high on this list. Champions League success for the Blues has been inconsistent throughout the years. In some seasons they surprise everyone, tumble every team, and sometimes get stuck in a round of 16 ties or in the group stage.

3. Porto – 10 losses

Many of you would’ve predicted FC Porto would be a name on this list. The Portuguese giants have frequently appeared in UCL knockouts, but have not been able to advance past the round of 16 more often. Although they are not as big as most of the other clubs in the league. They always put on a strong fight in the toughest of European competitions.

2. Arsenal – 13 losses

Arsenal are one of the teams that have been cursed for not being able to advance beyond the round of 16. In spite of not being able to qualify since 2016-17, their name remains on the list, proving their bad past. The Arsenal team might not have good numbers in the round of 16 but isn’t a team that should be taken lightly. Though they haven’t won the competition, they have been very close twice which makes the second in the list of most losses in the UCL Round of 16.

1. Real Madrid – 13 losses

Real Madrid are a name most of you would not have anticipated. The most successful team in the competition also has been a victim of the round of 16 traps. Madrid is a club that everyone predicts will reach at least the last eight every season, but big expectations also bring failures. Since 1992-93, they have suffered 13 losses the most in the UCL Round of 16.

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