The UEFA Champions League is certainly a magical tournament, which gives us plenty of emotion in each edition. It reunites the best teams in Europe to play for the most famous trophy in the world; therefore, it’s not a surprise when you see little teams doing the unthinkable in front of the favorites, having outstanding performances doing so.

Perhaps that’s not very common nowadays when you see very powerful squads taking care of business with relative ease, making all the way down the semi-finals or the final season after season, but in recent times we have witnessed some impressive upsets that surely shocked the world. We can say the most recent took place in Madrid a couple of days ago when Ajax took on Real Madrid and made 13-time winners look like an amateur team displaying one of the best games we’ve seen this season.

However, Ajax didn’t do anything new, as in the past we could see other teams with much less history than Ajax doing the unthinkable and upsetting teams that looked unbeatable at the time. Here are the worst Champions League upsets in history.

 

Dynamo Kiev vs. Real Madrid (1999)

The 1998-99 season was magical for Ukrainian side Dynamo Kiev, who saw how a very young and talented team made his way to the latter stages of Champions League by defeating great rivals. The perfect closing for of that season could have been winning the tournament, but nobody can tell they didn’t put a great effort in order to do so.

The highlight of their campaign was the elimination of Real Madrid in the quarter-finals, following a 1-1 draw in Spain that ended up with Dynamo dominating the Spanish side at Olympiyskiy Stadium, with a young Andriy Shevchenko introducing himself as a very promising striker. Unfortunately for the Ukrainians, they were eliminated by Bayern Munchen in the semi-finals, in which will be always remembered as the best Champions League campaign of the team.

 

Helsingborg vs. Inter (2000)

Back in August 2000, the Internazionale was looking to enter the Champions League group stage and the only thing between them and their goal was Swedish club Helsingborg. As you can imagine, not a single person believed the Swedish had a chance in front of the powerful Italians, but football once again proved nothing is written in this sport.

A late score by Michael Hansson in the first leg gave Helsingborg the advantage; an advantage they wouldn’t lose for anything. They reached the group stage after a 0-0 draw in San Siro the following week, leaving the Italian giants out of the Champions with an impressive performance in both matches.

 

Porto vs. Manchester United (2004)

Despite the fact that they received a little help from Roy Keane at the first leg, Portuguese team Porto knew how to disarm Manchester United in both games during the 2003/04 Champions League quarter-finals.

They won the first game 2-1 at home and entered the second one with more doubts than certain, but they knew how to respond when Paul Scholes scored the goal that could send the Red Devils to the semis. Tim Howard barely managed to stop Benni McCarthy’s free-kick and yet was unable to stop Costinha’s shot that took Porto to the next stage. Led by Jose Mourinho, that team won the Champions League in a great fashion, stating that they were ready to take it all no matter the rival or the venue.

 

Deportivo La Coruña vs. AC Milan (2004)

The 2003/04 Champions League was full of upsets and this case is another proof of that. It is never an easy job to play against the current champion of the competition and Deportivo La Coruña learned that the hardest way. They played at San Siro and got defeated by 4-1, with nearly zero hopes for any type of comeback in the second leg.

Little they knew that the victory was possible and the happiness was bigger when they embarrassed Milan at home, scoring three goals before half-time thanks to Walter Pandiani, Juan Carlos Valeron and Albert Luque. They finished the job in the second time thanks to a goal by captain Fran that sent Deportivo to the semi-finals, where they clashed with the eventual champions, Porto.

 

Schalke 04 vs. Inter (2011)

This has been one of the worst campaigns for a title holder in recent times and more when you see the bad moment the underdogs were having at that point. The German team was struggling to win in the Bundesliga and at the time of the game, nobody was expecting a good performance from them.

Well, they proved everybody was wrong when they trashed Inter at San Siro with a 2-5 win that improved Schalke’s form and showed that the magical Inter that won the tournament just a couple of months ago was gone. They finished the job at home with a 2-1 win.

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