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José Mourinho has singled out the Milan derby as the fixture that "surprised" him most throughout his coaching career, citing the unexpected lack of hostility between the two fanbases.
The 63-year-old is gearing up for his first Madrid derby in over a decade as Real Madrid prepare to take on Atlético this Sunday.
The clash represents the most significant challenge of Mourinho's second spell at the helm of Madrid to date. Away victories in this fixture have proven elusive in recent times, with Los Blancos claiming just one win from their last seven La Liga visits to the Metropolitano.
A positive result would strengthen Madrid's standing as genuine title contenders this campaign, while a loss would drop them below their city rivals in the standings.
Although it has been some time since his last involvement in this fixture, Mourinho is well-acquainted with intense, high-stakes atmospheres, having managed derbies—and actively fueled the tension—in Manchester, Milan, Rome, London, Istanbul and Lisbon, as well as the Clásico.
'In Portugal That's Impossible'—Mourinho's Milan Derby Surprise
When asked at his pre-match press conference what derby day means to him, Mourinho told the media: "A derby always carries something extra.
"Derbies are about history, culture, the passion of the supporters, players, coaches ... of those who quickly grasp what it truly means. But ultimately, it's still a three-point game."
Mourinho went on to reveal how, during his time at Inter Milan, he was taken aback to find that the Milan derby is in fact a rather "friendly" rivalry.
"It's difficult to say [which derby affected me the most]," he said. "Because when you put on a club's shirt, you begin to feel like a supporter yourself. There isn't a derby where you're walking down the street the week before and someone doesn't say to you, 'We're going to destroy Juve...' or whoever.
"The one that surprised me most because it was so unexpected was Milan-Inter, because I expected there to be ... not a great deal, but at least some hatred, and I was caught off guard by how friendly they are, how well they get along.
"The real animosity is a bit further north [with Juventus]. I'd see a woman and a man walking down the street wearing their different shirts, or a father and a child together. In Portugal that's impossible ... and in Türkiye, don't even get me started!"
Mourinho's Recent Record in Derbies
Mourinho's final Madrid derby ended in heartbreak, with Los Blancos suffering a 2–1 extra-time defeat to Atleti in the 2012–13 Copa del Rey final. Just two days later, Real Madrid and Mourinho confirmed they would go their separate ways at the season's conclusion.
Since that point, Mourinho has remained a central figure in some of the most heated local rivalries across the continent.
In the immediate aftermath of his first Madrid departure, Mourinho's derby form remained impressive, with his Chelsea side going unbeaten against Arsenal across five encounters—including a stunning 6–0 thrashing of the Gunners during the 2013–14 season.
At Manchester United, Mourinho managed just one Premier League win in four meetings against Manchester City as his team struggled to match their crosstown rivals. Nevertheless, he did engineer a memorable 3–2 triumph over Pep Guardiola's side late in the 2017–18 season that briefly disrupted his rivals' title celebrations.
During his tenure as Tottenham Hotspur manager, he defeated Arsenal twice in four encounters, but was unable to get the better of his former club Chelsea.
Across five Rome derbies, Mourinho's Roma managed to overcome Lazio on just one occasion, while he failed to defeat either Beşiktaş or Galatasaray during a turbulent stint in Türkiye.
Most recently, back in Portugal last season, his Benfica side enjoyed a remarkable unbeaten 2025–26 campaign, picking up four points from six available against Sporting CP.