Yet the Portuguese was put in his place by Borussia Dortmund boss Jurgen Klopp on Wednesday evening as the Bundesliga side recorded a 4-1 win over Madrid in the first-leg of their Champions League semi-final.
It was not the first time that the 50-year-old was on the wrong end of a shock result during his coaching career, though.
Goal.com delves into the past of the 'Special One' and singles out five of his most remarkable - although not necessarily the biggest - defeats until this week's humiliation at Signal Iduna Park.
|MARITIMO 3-0 BENFICA, NOVEMBER 2000
Mourinho had started the season as Jupp Heynckes' assistant, but took over from the German just four games into the 2000-01 campaign. The start of his coaching career would not go entirely according to plan, though, as he started with a loss against Boavista, before his Benfica were humiliated by Maritimo only weeks later. Despite having stars such as Robert Enke, Carlos Marchena, Maniche and Pierre van Hooijdonk at his disposal, Mourinho's Benfica were beaten 3-0, as Argentine attacker Carlos Lagorio netted a hat-trick in Funchal. His spell in charge of the Lisbon giants would come to an end after just nine games as he resigned after the club refused to offer him a new contract.
|PORTO 0-1 PANATHINAIKOS, MARCH 2003
Mourinho would win his first major titles with Porto and it was their successes in Europe in particular that attracted the interest of the continent's elite. Nevertheless, the Portuguese giants nearly missed out on Uefa Cup glory after a shock 1-0 defeat in the first leg of the quarter-final tie against Panathinaikos. Emmanuel Olisadebe's 72nd minute goal proved to be the difference in the first leg to upset Mourinho's men. Fortunately his side bounced back in the return leg as they recorded a 2-0 away win.
|MIDDLESBROUGH 3-0 CHELSEA, FEBRUARY 2006
After joining Chelsea in the summer of 2004, Mourinho had turned the Londoners into a well-oiled machine that cruised to Premier League glory in 2005 and 2006. Nevertheless, the Portuguese coach did have some difficult moments in England's top flight as well. After beating Liverpool 2-0 the week before, Chelsea were brimming with confidence ahead of the away game against Middlesbrough. They would soon be brought back down to earth, though, as they were heavily beaten 3-0. Fabio Rochemback opened the scoring after just two minutes, before Stewart Downing and Yakubu piled even more misery on Chelsea.
|SAMPDORIA 3-0 INTER, MARCH 2009
In only his first season at Inter, Mourinho appeared to be cruising towards a domestic double. The Nerazzurri comfortably sat atop of the Serie A table and were paired with Sampdoria in the semi-finals of the Coppa Italia. However, Inter's dreams of winning the double were ended abruptly by Samp as they effectively decided the two-legged tie within the first 45 minutes. Antonio Cassano broke the deadlock early on, with Giampaolo Pazzini adding two more before half-time in the first leg. Inter would win the return 1-0, but it was not enough for the Giuseppe Meazza outfit.
|BARCELONA 5-0 REAL MADRID, NOVEMBER 2010
In what was arguably the biggest test since his move to Madrid in the summer of 2010, Mourinho's men travelled to Camp Nou for his first Clasico in November 2010. However, despite his high expectations ahead of the game, it would prove to be a match to forget for the 50-year-old. The Catalans were on top right from the start and goals from Xavi and Pedro gave them a two-goal lead at half-time. Things would only get worse for Madrid after the break as David Villa netted a double, before Jeffren put the icing on the cake in the closing stages of the game to make it five.