He’s had to take the rough with the smooth.

Jose Mourinho endured one of his worst nights as Manchester United manager on Wednesday as his side fell to a 2-1 defeat to Bristol City in the Carabao Cup quarter-final.

While Manchester City, Arsenal and Chelsea all booked their places in the last four, United were humbled by a spirited display from the Robins in front of an elated Ashton Gate.

Mourinho bemoaned his side’s lack of intensity and, while all credit is due to Bristol and their manager Lee Johnson, the result has to rank among the Portuguese coach’s most embarrassing.

It doesn’t come close to the humiliation of Louis van Gaal’s United getting hammered 4-0 by MK Dons in the same competition three years ago, but it’s still one of the darker days Mourinho has experienced in charge of the Red Devils.

Here are five other times he has been humbled.

Borussia Dortmund 4-1 Real Madrid (April 2013)

Mourinho endured a painful 2012/13 season with Madrid. They lost to rivals Atletico Madrid in the Copa del Rey final and were distinctly second-best in the La Liga title race, finishing 15 points behind Tito Vilanova’s Barcelona.

It all ended in tears in Europe, too, as Real were comprehensively undone by a Robert Lewandowski-inspired Dortmund. The Polish striker scored all four goals as Jurgen Klopp’s gegenpressing outfit hammered Mourinho’s men 4-1 in the Champions League semi-final first leg.

It was actually the second time that season Madrid had fallen to Dortmund, also losing 2-1 when they travelled to the Westfalenstadion during the group stages. But the semi-final battering particularly stung as it effectively ended Mourinho’s hopes of European dominance that season.

Barcelona 5-0 Real Madrid (November 2010)

Mourinho enjoyed an excellent start to his reign as Madrid boss, taking 32 points from a possible 36 in his first dozen league games. So he arrived at the Camp Nou in buoyant form, not expecting to receive an absolute lashing from Pep Guardiola’s Barca.

David Villa struck twice in the five-goal rout as Barcelona dominated the game from beginning to end. “They could have played with two balls,” Marca journalist Roberto Palomar wrote, “and Barcelona would have controlled both.”

Mourinho has suffered a few ignominious defeats at the hands of Guardiola, but that night in the Camp Nou remains the most helpless he has ever looked on a touchline.

Middlesbrough 3-0 Chelsea (February 2006)

By the end of a rare defeat in his second season at Chelsea, Mourinho would have heard the Boro fans chanting ‘we want seven.’ It was a result that shook the Premier League as the Blues had tasted defeat just once in their 25 league games that season (away to Manchester United).

But they were thumped by Steve McClaren’s Boro at the Riverside, going down to goals from Fabio Rochemback, Stewart Downing and Yakubu. It was Mourinho’s heaviest defeat since being appointed Blues boss 20 months earlier – it’s a good thing the linesman ruled out Boro’s fourth for offside.

Chelsea 4-0 Manchester United (October 2016)

As far as reunions with former employers go, this was utterly disastrous. From the moment Pedro scored after 29 seconds Chelsea had their way with a remarkably poor United. Unfortunately for Mourinho, this was just when Chelsea were gloriously clicking into gear under Antonio Conte, who had switched to a three-man defence after losing 3-0 to Arsenal in September.

The Blues were simply too good, too fast and too smart for an accident-prone United. Mourinho lost at Stamford Bridge again this season, but it was nowhere near the horror show of this four-goal drubbing.

Atalanta 3-1 Inter Milan (January 2009)

Mourinho’s Inter romped to the Serie A title during his debut season in Italy, clinching the Scudetto by ten points. However, there were hitches along the way, none more harrowing than a wretched display away to Atalanta, who failed to escape relegation that season.

The Nerazzurri were a resolute defensive unit under Mourinho, so it came as quite a surprise to see such an error-strewn performance inside the Stadio Atleti Azzurri d’Italia. It could have been more, too, with Atalanta missing a string of chances.

Mourinho said his players made ‘horrible mistakes’ afterwards. Club president Massimo Moratti said it was impossible for them to have been any worse. That says it all really.

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