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Despite dividing opinion, Jose Mourinho is undeniably one of the best managers in the game. From being an unsuccessful player to having a brimming trophy cabinet as a manager, Mourinho perfectly epitomises his 'the special one' sobriquet.
His charisma, coupled with his unique management style, has helped him earn success in multiple countries. However, it was at Porto where he first rose to prominence.
Porto struggled before his arrival in 2002. But the AS Roma manager, with his distinct quick-pressing style of football brought trophies galore to the club. Their stunning Champions League triumph in 2004 made headlines, catapulting Mourinho into the big league.
Mourinho subsequently enhanced his reputation and pedigree at Chelsea, Inter Milan, Real Madrid and Manchester United. He is one of a handful of managers to win the Champions League with multiple clubs (Porto, Inter). Mourinho has also won league titles in three different countries (Portugal, England, Spain).
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However, things haven't always been rosy for Mourinho. He has had to experience some slumps. The Portuguese tactician, despite being exceptional, has been outdone by other managers on numerous occasions.
On that note, here's a look at the five biggest defeats the Portuguese has endured in his managing career thus far:
#5 Chelsea 0-3 Middlesbrough (Premier League, 2006)
Chelsea brought in Jose Mourinho in 2004 following his exploits at Porto. They perceived him as the right person to lead them into a new era.
Mourinho vindicated that decision as Chelsea became a dominant force in English football under his tutelage. The Blues won consecutive Premier League titles (2004-05 and 2005-06) to announce themselves as a force to be a reckoned with.
However, they experienced a shock defeat during this indomitable period. Chelsea were humbled 3-0 by Middlesbrough in a Premier League game in 2005-06 season. This was only the third loss Mourinho in 64 games Mourinho endured after arriving at Chelsea.
Capitalising on the Blues' lousy defending and riding on a magnificent strike from Yakubu, Middlesbrough registered a memorable win. This was also the biggest defeat of Mourinho's managerial career at that time.
#4 Borussia Dortmund 4-1 Real Madrid (Champions League, 2013)
Robert Lewandowski is one of the top strikers in the game at the moment. However, it was at Borussia Dortmund where he first made his name.
During the Champions League semis in 2012-13 against Real Madrid, a stunning Lewandowski quadruple sunk the illustrious visitors in the first leg in Dortmund. Mourinho's men only managed a 2-0 win in the return to be knocked out on aggregate.
That defeat essentially ended Jose Mourinho's managerial stint at Real Madrid. Los Blancos were a star-studded team, and were the better team on paper compared to Borussia Dortmund.
However, despite their inexperience and gulf in pedigree, Jurgen Klopp's men dismantled the Spanish giants. Lewandowski scored all four goals on that historic night, becoming the first player to do so in a Champions League semi-final.
Lewandowski also became the first player to score a hat-trick against Real Madrid in the continental competition. In the process, Jose Mourinho was also handed his biggest loss in the Champions League.
Although Real Madrid fought back in the second-leg, their comeback fell short as Dortmund booked an all-German final with Bayern Munich.
Following the defeat, Mourinho's relationship with his players deteriorated. He resigned from the club at the end of the season. The final nail in his coffin was struck by Atletico Madrid, who beat Madrid 2-1 in the Copa del Rey final that campaign.
#3 Chelsea 4-0 Manchester United (Premier League, 2016)
Jose Mourinho was signed by Manchester United right after he was sacked by Chelsea following his second spell with them. That came as a shock to the London club's fans. However, they did not have to wait long to voice their frustration with the person who won them their first Premier League title.
Both United and Chelsea endured bumpy starts to their league campaigns that season. So both teams needed a win when the Red Devils visited Stamford Bridge in October 2016. However, it was Chelsea who had the last laugh as Jose Mourinho's side endured a hiding.
The Blues opened the floodgates after just 30 seconds as they scored four unanswered goals past Manchester United. It was Mourinho's heaviest Premier League defeat at the time.
In a far from memorable return to Stamford Bridge for Mourinho, the Chelsea fans chanted 'you're not special anymore', adding insult to injury.
#2 Barcelona 5-0 Real Madrid (La Liga, 2011)
While a defeat in El Clasico is bitter, imagine being humiliated! That is exactly what happened when Jose Mourinho's Real Madrid went head-to-head against a formidable Barcelona team.
Jose Mourinho had only recently taken charge of Real Madrid following his treble-win with Inter Milan in 2009-10. Madrid were undefeated in La Liga before clashing with Barcelona. What was expected to be a thrilling fixture against two great teams managed by two fine managers turned out to be a damp squib - a lopsided affair.
In Mourinho's first El Clasico game in charge, the Blaugrana scored five goals without reply. Surprisingly, Mourinho kept his job that year and won Madrid's first league title in four years in 2012. He won a few trophies before parting ways with the club in 2013.
#1 FK Bodo/Glimt 6-1 AS Roma (Europa Conference League, 2021)
Jose Mourinho's latest managerial endeavour saw him join AS Roma this summer after a disappointing end to his stint at Tottenham Hotspur last year. He started the 2021-22 campaign on a positive note. His team grabbed a sensational last-minute victory in Mourinho's 1000th managerial game in charge; Roma won that Serie A game 2-1. However, things quickly went south from there.
Eight games later, Mourinho suffered the biggest defeat of his managerial career. A much-changed Roma were routed 6-1 in the inaugural UEFA Europa Conference League by an unheralded FK Bodo/Glimt side.
Glimt had only won the Norwegian league for the first time in their history last season.
However, none expected them to beat a formidable AS Roma side, certainly not in the manner in which they did. Glimt's best-ever previous performance in Europa was a first-round appearance in the UEFA Cup, which they've done three times.
A defeat was never on the books for Mourinho's team. However, Glimt scored three in the first half to turn the game on its head. Any hope of a Roma comeback was thwarted by Glimt, who scored three more in the second half. Carles Perez's first-half strike for Roma was only a consolation on the night.
