Jose Mourinho’s Record vs. Real Madrid

When Real Madrid pivoted to José Mourinho in 2010, with the Portuguese’s stock at an all-time high, he was tasked by Florentino Pérez with one thing: stop Pep Guardiola.

It would take a battering in his first Clásico, mass psychological warfare, and the alienation of Madrid icons, but Mourinho would eventually stymie Barcelona’s mastery with a record-breaking La Liga triumph in 2011–12.

Mourinho, at his apex, relished the manifestation of footballing evil against the supposed "good guys" of Catalonia, but the division he’d ignited proved too much to bear after a third season in charge. Borussia Dortmund’s rout of Madrid in the 2012–13 Champions League semi-finals represented a shifting of the guard at the summit of the European game, and Mourinho was soon back to winning Premier League titles with Chelsea.

While there have been sporadic calls for Mourinho’s return in the decade or so since his departure, Real Madrid have seldom encountered their former manager. However, his history with Los Blancos dates back to his glorious Porto days.

Mourinho’s Results Against Real Madrid

Outcome	Number of Games
Mourinho Wins	0
Real Madrid Wins	4
Draws	1

Real Madrid 1–0 Porto (February 19, 2002)

Zinedine Zidane — Mourinho’s first clash against Madrid ended in defeat. | CHRISTOPHE SIMON/AFP/Getty Images)

Mourinho wasn’t even a month into the Porto job when he faced Real Madrid for the first time.

Porto struggled during the first half of 2001–02 under Octávio Machado, with Mourinho inheriting a side that sat bottom of their group in the second group stage of that season’s Champions League.

A trip to the Santiago Bernabéu was thus daunting for the Portuguese side, but they were seven minutes away from earning an impressive point before substitute Santiago Solari struck. Their stubbornness under Mourinho was clear from the outset, with Porto able to flummox a Madrid team that had been so free-scoring in the weeks leading up to the contest.

Porto 1–2 Real Madrid (February 27, 2002)

Porto were again impressive in the reverse fixture a week later, although Madrid were without the likes of Luís Figo and Zinedine Zidane.

Vincente del Bosque’s makeshift lineup, which included the usage of Guti as a withdrawn centre forward, got off to a brilliant start. Goals from Solari and Iván Helguera helped them into a 2–0 lead, but Porto were superior after Capucho halved the deficit before the half-hour mark.

Mourinho would later phase out the experienced forward and move him on after the 2002–03 campaign, but Capucho was one of the key figures of Mourinho’s first Porto team. Madrid held on for a hard-fought away win, and Del Bosque’s side would go on to conquer the continent courtesy of some Zidane magic in Glasgow.

Porto 1–3 Real Madrid (October 1, 2003)

Luís Figo — Madrid toppled Mourinho’s Porto in the 2003–04 group stage. | JAVIER SORIANO/AFP/Getty Images

Porto headed into 2003–04 as Portuguese and UEFA Cup champions, but there was no sense that Mourinho’s maturing side were capable of toppling the continent’s aristocracy.

That belief was further backed when Madrid defeated Porto 3–1 in their own backyard on Matchday 2 of the group stage. Porto had been held to a point by Partizan Belgrade in their Group F opener, and they were eventually overwhelmed by Madrid’s "Galácticos" after taking an early lead through a Costinha header.

Helguera and Solaria, far from superstars, were on the scoresheet again for the away side before Zidane sealed Madrid’s victory with a clever finish from a well-worked free-kick.

Real Madrid 1–1 Porto (December 9, 2003)

Deco — Porto finally secured a result against Madrid at the fourth attempt under Mourinho. | Etsuo Hara/Getty Images

When the two teams met again at the end of the group stage, both have secured their spots in the round of 16. The unbeaten Madrid were group winners, while Porto failed to taste defeat after the opening matchday.

Still, the stars were out for what was really a dead rubber, and Mourinho was able to secure his first result against Los Blancos at the fourth time of asking. Solari once again found the net in this fixture, but his early strike was cancelled out by a Derleí penalty and the spoils were shared.

Porto’s second-place finish in Group F left them as big underdogs for their round of 16 clash with the mighty Manchester United.

Real Madrid 2–1 Man Utd (August 8, 2017)

Cristiano Ronaldo, José Mourinho — Mourinho’s Man Utd were beaten in the UEFA Super Cup. | Angel Martinez/Real Madrid/Getty Images

Before Mourinho returned to Portugal with Benfica, he’d faced his former employers just once since his departure in 2013.

The Portuguese had garnered a lofty reputation for his capacity to adopt masterful game plans for one-off occasions, but never before had he lifted the UEFA Super Cup when his Manchester United side faced Real Madrid, European champions for the third time in four years, in 2017.

Mourinho masterminded United’s Europa League final triumph over Ajax, setting up this fixture in Skopje, North Macedonia.

Cristiano Ronaldo started on the bench for Zidane’s side, and wouldn’t feature until the 82nd minute. By that point, Madrid had seen their 2–0 lead halved by Romelu Lukaku—the Red Devils’s big-money signing of the summer—but they held out for another piece of silverware. As a result, Mourinho became the first manager in history to lose three UEFA Super Cup matches.

Nevertheless, the United boss said he left Skopje "optimistic and proud" for the season ahead.