The Spaniard has been outclassed time and again by different teams and managers.

Having managed the likes of Barcelona, Bayern Munich and Manchester City so far in his career, Josep “Pep” Guardiola will go down as one of the best managers that the world of football has ever seen. He has won league titles in Spain, Germany and England multiples times, and also the UEFA Champions League (twice), FIFA Club World Cup (thrice) and the UEFA Super Cup (thrice).

Pep Guardiola has led his teams in a total of 627 matches across all competitions, out of which he won 466 and lost only 73 – which implies that defeats come rarely for the Spaniard. That being said, some of the games which he has lost hold special places in the history of the game.

Without further ado, let’s take a look at the top ten occasions when Guardiola’s teams were humiliated by their opponents:

10. Manchester United 2-0 Manchester City (March 8, 2020)

Pep Guardiola’s most recent game with Manchester City in the Premier League was against arch-rivals Manchester United, and it ended in a defeat. With both Kevin De Bruyne and Aymeric Laporte sidelined due to injuries, City looked lifeless during a major portion of the game.

The defeat highlighted Manchester City’s defensive capabilities

Ole Gunnar Solskjaer’s men opened the scoring through Anthony Martial in the 30th minute. He remained unmarked as Bruno Fernandes’ dinked free-kick came into the Cityzens‘ penalty box, and all he had to do was to beat goalkeeper Ederson. In the 90th minute, it was Ederson’s turn to commit a howler himself as he collected the ball and threw it straight back at United’s Scott McTominay, who then found the empty net from 40 yards out.

The eventual outcome of this rivalry was fairly inconsequential for City given the fact that they were way behind table-toppers Liverpool, but it highlighted the defensive problems in Guardiola’s “world-beating” side.

9. Tottenham Hotspur 1-0 Manchester City (April 9, 2019)

In the 2018-19 season, Tottenham did not have much success in the Premier League, finishing at the fourth place a whopping 27 points behind champions Manchester City. Hence, when both teams got drawn against each other in the Champions League quarter-final, most fans predicted that Pep Guardiola and co would easily walk into the next round.

Guardiola’s side failed to score an away goal

However, that was not to be – as Sergio Aguero missed a penalty just 13 minutes after kick-off and Son Heung-min found the winner for the North Londoners in the second half. City’s inability to score an away goal would eventually prove to be costly, as they won the second-leg 4-3 but still failed to progress to the semi-final with the aggregate score reading 4-4.

Manchester City thus had to wait for atleast another year to contest for European glory, and the magnitude of the defeat was so heavy that fans started criticizing Guardiola despite him leading them to a domestic treble in the same campaign.

8. Liverpool 3-1 Manchester City (November 10, 2019)

It would not be wrong to say that this was the game in which Manchester City lost their Premier League title race this season. Prior to the match, they were only six points behind Liverpool, but the Reds won 3-1 resulting in them gaining three more points over their arch-rivals.

One should note that City did not really play poorly in defeat – however, defensive mishaps and a lack of cutting edge in key moments cost them dearly while pushing Jurgen Klopp’s boys towards their first league title in 30 years.

The loss also served as the point of no return for the Sky Blues, although it was just November at that point and a few more months were remaining till the end of the season – as Liverpool kept extending their lead over them to 25 points until March, when the season got suspended by the global outbreak of COVID-19.

7. Wolfsburg 4-1 Bayern Munich (January 30, 2015)

Bayern Munich has been a force to reckon with in the Bundesliga over the past many years. When Pep Guardiola was appointed their manager in 2014, their performances stepped up another notch – which is why their defeat against Wolfsburg was shocking and embarrassing for both him and his club.

The six-week winter break in Germany had just ended, and Guardiola’s side who looked to resume their winning ways from before Christmas were left for dead by Wolfsburg. Bas Dost and Kevin De Bruyne (who would later play under the Spaniard at Manchester City) each scored twice as Bayern Munich suffered a first meaningful loss in more than two years.

However, the defeat did not stop the Bavarians from winning the title at the end of the season.

6. Norwich City 3-2 Manchester City (August 14, 2019)

​​Norwich City themselves would consider this as their greatest result in the history of their Premier League appearances. The defeat was also an indicator for defending champions Manchester City that they were going to encounter more than a few difficulties this season.

The win was Norwich City’s one of the highlights of the Premier League

Both Nicolas Otamendi and John Stones did their best to convince Pep Guardiola that they did not deserve starting chances at the club, as the Canaries romped home to a 3-2 victory in front of their home fans. Given the fact that they are currently languishing at the bottom of the table with just five wins from 29 matches, you can understand how embarrassing it is for City to have lost against them.

Needless to say, the defeat which could have been avoided left another dent into the Cityzens‘ title hopes this season.

5. Monaco 3-1 Manchester City (March 15, 2017)

In the 2016-17 season, Manchester City finished at third place in the Premier League, and their overall campaign in England was average considering their standards in more recent times. Pep Guardiola hence decided to focus solely on the Champions League as he himself announced during a press conference at that time, but that could not happen either – thanks to AS Monaco in the round of 16.

The Ligue 1 side had been quite the dark horses both in France and in Europe throughout the season, and they claimed another scalp by beating Manchester City 3-1 to overturn a crazy 5-3 first-leg deficit in remarkable style. The likes of Kylian Mbappe, Fabinho and Radamel Falcao scored for them over the two legs, but it was the English side’s defensive frailties that cost them more, as they failed en route to what could have been their first-ever UCL trophy win.

4. Liverpool 3-0 Manchester City (April 4, 2018)

After Manchester City’s defeat to Monaco in 2017, we had to wait for more than one year to see them making another mistake. But when it happened – against Liverpool, once again in the Champions League – it looked really bad for them.

The match was regarded as one of the best games of the UCL that year

The Reds playing in their own backyard showed no mercy on the Cityzens, as they flew to a 3-0 lead within 31 minutes after kick-off in the quarter-finals first leg. They then set out to save their lead, and their desire and unflinching work ethic proved too much for Guardiola as he had no solution in hand. He even played newly-signed Aymeric Laporte at left-back in a bid to have all his best defenders on the pitch at the same time, but it only looked extremely foolish in the end.

City eventually got eliminated from the competition, as they lost the second leg as well by a scoreline of 2-1.

3. Everton 4-0 Manchester City (January 15, 2017)

It is extremely impossible to think that Manchester City would lose by a big margin to a side like Everton. However, it did happen only a little over three years ago.

City’s defensive issues came to light once again as the Toffees tore them apart. Romelu Lukaku and Kevin Mirallas helped Everton ease to a 2-0 lead by the 50th minute, and in the last ten minutes, a then-unknown Tom Davies and Ademola Lookman scored their first-ever league goals in England to add salt to the Sky Blues’ wounds.

Arguably, this is the worst result and performance from the Cityzens in the Pep Guardiola era, and what is more frightening is that Nicolas Otamendi who led their erroneous defense back then, is still playing on a weekly basis for them.

2. Inter Milan 3-1 Barcelona (April 20, 2010)

Pep Guardiola’s time with Barcelona can be regarded as one of the most glorious manager-club partnerships in the history of the sport – and that is why the Blaugrana‘s defeat against Jose Mourinho’s Inter Milan in the semi-finals of the 2009-10 Champions League can be regarded as one of his worst defeats ever.

Inter advanced to the final despite a 1-0 loss in the second leg

Through Pedro in the 19th minute, the Catalans raced to a 1-0 lead but Wesley Sneijder, Maicon and Diego Milito scored for the Nerazzurri. Barcelona’s tactical failures resulted in both Maicon’s and Milito’s goals, as Pep Guardiola showed signs of losing focus after they conceded Sneijder’s equalizer. He pushed the team to attack more, resulting in massive holes in their back-line. Inter exploited them neatly to win the game.

The two-goal difference proved vital for Mourinho’s side in the second leg, as they advanced to the finals despite a 1-0 loss (they won 3-2 on aggregate)

1. Real Madrid 4-0 Bayern Munich (April 29, 2014)

Pep Guardiola himself revealed in an interview that this has to be his worst defeat of all time, as Real Madrid made themselves look like men against boys while playing against Bayern Munich in the 2013-14 Champions League semi-final. Having lost the away leg 1-0, all the Bavarians had to do under the Spaniard was to win with a lead of at least two goals at home in the second leg.

The Spaniard later revealed defeat against Real Madrid was his worst defeat of all time

But Los Blancos had other plans as Sergio Ramos scored twice and Cristiano Ronaldo added another for them to race to a 3-0 lead by half-time. Ronaldo scored once again late in the second half to complete a 5-0 aggregate triumph for Guardiola’s once familiar adversaries.

Having led Barcelona to multiple wins against Real Madrid, one would feel that the Spaniard should have won this one too. But failures in arranging Bayern’s defence and preparing for facing Cristiano Ronaldo resulted in an embarrassment that would haunt him throughout his life.

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