Jose Mourinho's Battle History Against Real Madrid Revealed

When Real Madrid turned to José Mourinho in 2010, with the Portuguese coach's reputation at its peak, Florentino Pérez assigned him a singular mission: halt Pep Guardiola's dominance.

It required enduring a crushing defeat in his inaugural Clásico, engaging in extensive mind games, and distancing himself from Madrid legends, but Mourinho would ultimately break Barcelona's stranglehold with a record-setting La Liga victory in 2011–12.

Mourinho, in his prime, embraced playing the role of football's villain against Catalonia's perceived "heroes," yet the discord he created became unbearable after three seasons at the helm. Borussia Dortmund's demolition of Madrid in the 2012–13 Champions League semifinals marked a changing of the guard at European football's pinnacle, and Mourinho soon returned to claiming Premier League trophies with Chelsea.

Though there have been occasional demands for Mourinho's comeback in the decade following his exit, Real Madrid have rarely crossed paths with their former coach. Nevertheless, his connection with Los Blancos traces back to his triumphant Porto era.

Mourinho's Results Against Real Madrid

Mourinho's Results Against Real Madrid

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

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

Mourinho had barely completed a month at Porto when he encountered Real Madrid for the first time.

Porto had struggled throughout the opening half of 2001–02 under Octávio Machado, leaving Mourinho with a squad languishing at the bottom of their Champions League second group stage pool.

A journey to the Santiago Bernabéu therefore seemed intimidating for the Portuguese outfit, yet they came within seven minutes of securing a remarkable draw before substitute Santiago Solari found the net. Their resilience under Mourinho was evident immediately, as Porto managed to frustrate a Madrid squad that had been prolific in recent matches.

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

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

Porto delivered another strong performance in the return leg one week later, despite Madrid missing key players like Luís Figo and Zinedine Zidane.

Vicente del Bosque's improvised formation, featuring Guti deployed as a deep-lying striker, began superbly. Strikes from Solari and Iván Helguera established a 2–0 advantage, but Porto dominated after Capucho reduced the margin before the thirty-minute mark.

Mourinho would subsequently sideline the veteran attacker and transfer him following the 2002–03 season, though Capucho remained a crucial component of Mourinho's initial Porto squad. Madrid preserved their narrow away victory, and Del Bosque's team would later claim continental glory through Zidane's brilliance in Glasgow.

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

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

Porto entered 2003–04 as Portuguese and UEFA Cup winners, yet few believed Mourinho's developing team could challenge Europe's elite clubs.

This perception was reinforced when Madrid crushed Porto 3–1 on their home turf during the second group stage matchday. Porto had managed only a draw against Partizan Belgrade in their Group F debut, and they were ultimately overpowered by Madrid's "Galácticos" despite grabbing an early advantage through Costinha's header.

Helguera and Solari, hardly household names, again scored for the visitors before Zidane clinched Madrid's triumph with an intelligent finish from a well-executed set piece.

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

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

When both sides clashed again at the group stage conclusion, each had already qualified for the knockout rounds. The perfect Madrid topped the group, while Porto remained undefeated following their opening match.

Despite this being essentially a meaningless encounter, the star players participated, and Mourinho finally achieved his first positive result against Los Blancos on his fourth attempt. Solari scored yet again in this matchup, but his early goal was neutralized by a Derleí spot-kick, resulting in a shared outcome.

Porto's runner-up position in Group F made them heavy outsiders for their round of 16 encounter against the formidable Manchester United.

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

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

Prior to Mourinho's return to Portugal with Benfica, he had confronted his former club only once since leaving in 2013.

The Portuguese had built a distinguished reputation for devising brilliant tactical approaches for crucial matches, yet he had never claimed the UEFA Super Cup when his Manchester United team met Real Madrid, European champions for the third time in four seasons, in 2017.

Mourinho orchestrated United's Europa League final victory over Ajax, earning this encounter in Skopje, North Macedonia.

Cristiano Ronaldo began among the substitutes for Zidane's team, only entering in the 82nd minute. At that stage, Madrid had watched their 2–0 cushion reduced by Romelu Lukaku—the Red Devils' expensive summer acquisition—but they maintained their advantage to secure another trophy. Consequently, Mourinho became the first coach ever to suffer three UEFA Super Cup defeats.

Despite this, the United manager stated he departed Skopje feeling "optimistic and proud" about the upcoming campaign.