Liverpool, Villarreal & more: The five biggest upsets in Champions League history

The 2021/22 Champions League knockout stages have produced one of the biggest upsets in the history of the competition.

The upset would occur in the quarter-finals and saw Spanish outfit Villarreal knock German powerhouse Bayern Munich out of the Champions League after picking up a 1-0 win in the first leg and then holding out for a draw in the reverse fixture to secure their spot in the semi-finals.

After such a historic night for Villarreal, 101 have decided to take a look back at the five biggest upsets in the history of the Champions League.

5. Ajax vs Real Madrid, Round of 16 (2019)

Real Madrid are the undisputed kings of the Champions League, winning the competition a record 13 times, including three on the bounce from the 2015/16 campaign to the 2017/18 campaign.

However, their reign of dominance was ended in 2018/19 by a very unlikely side.

Madrid took on Ajax in the Round of 16 that season, picking up a 2-1 win in the first leg in Amsterdam.

So, it was expected that the Spanish powerhouse would have little issue seeing off a relatively unknown Ajax once again at the Bernabeu.

However, this was not the case, and Erik ten Hag’s side would go on to beat Los Blancos by four goals to one at their home ground – a historic win and one that was part of a memorable season for a now weakened Ajax team.

4. AS Monaco vs Real Madrid, Quarter-final (2004)

As already discussed above, Real are one of the most feared sides in European football.

And in 2004 they once again had a sensational squad that featured the likes of Ronaldo, Luis Figo, Iker Casillas and Zinedine Zidane.

With such quality players, it was not at all surprising when Real took a 5-2 aggregate lead in the second leg against Monaco.

However, in a spectacular second-half comeback, Monaco brought the tie back to 5-5 and went through on away goals.

3. Liverpool vs AC Milan, Final (2005)

In current times Liverpool seeing off AC Milan is not at all surprising, with Jurgen Klopp’s side picking up two wins over the Italian outfit already in 2021/22.

Back in 2005, though, it was very different story. Milan boasted one of the best teams in world football, as showcased by their starting eleven from the final:

AC Milan XI: Dida, Cafu, Jaap Stam, Alessandro Nesta, Paolo Maldini, Pirlo, Gennaro Gattuso, Clarence Seedorf, Kaka, Andriy Shevchenko, Hernan Crespo.

In comparison, Liverpool had one or two world-class talents in the form of Steven Gerrard and Xabi Alonso, but the rest of their squad was full of solid, but not great players.

Despite this, and the fact they went 3-0 down, Liverpool were able to bring the score back to level terms in 90 minutes before winning the penalty shootout.

2. Villarreal vs Bayern Munich, Quarter-finals (2022)

The next name on our list is the most recent upset in the Champions League.

Bayern Munich have developed a reputation over the last several years for really punishing sides who are either lesser established at this level - e.g. Salzburg in the last round when they put seven past them - or big sides that are not on their game, such as FC Barcelona who were beaten 8-2 by Bayern in 2020.

So, when the Bavarian powerhouse were drawn against a Villarreal team who are relativity unproven at this level – only making it to the semi-finals of the Champions League once in their history before this season -  it was expected Bayern would notch something of a cricket score vs Unai Emery and co.

However, the Spanish side beat Bayern 1-0 in the first meeting between the pair and then snatched a late equaliser in the return leg to secure their spot in the semi-finals.

1. Sheriff vs Real Madrid, Group stage (2021)

Whilst the rest of the games on our list are perhaps more impressive achievements as they took place over two legs of knockout football, Sheriff’s win over Real Madrid still remains one of the most shocking upsets in Champions League history.

Sheriff had never made it to the Champions League group stages before 2021/22, becoming the first Moldovan team to do so after seeing off Dinamo Zagreb in a qualifier.

Yet, despite having basically no European pedigree, Sheriff were able to pick up a 2-1 win over now semi-finalists Real Madrid in this season’s group stages.

Sheriff went on to fall out of the CL into the Europa League where they were knocked out by Braga. But their win against Real will still no doubt live long in the memory of their fans.

Read more:

Liverpool vs Benfica betting tips: Champions League quarter-final second leg preview, predictions and odds

Rangers vs Braga betting tips: Europa League quarter-final second leg preview, predictions and odds


Josh Barker

Josh Barker

Middlesbrough fan from the North East of England. @JoshBarker979 on Twitter.

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