Can Mourinho finally break his 24-year Bernabéu curse against Real Madrid tonight?

Tonight, José Mourinho faces a high‑stakes, all‑or‑nothing showdown against his old club, Real Madrid—now coached by one of his former players, Álvaro Arbeloa. Arbeloa has openly called himself a proud “Mourinhista.” It’s master versus apprentice, and the drama practically writes itself.

But Mourinho’s return to what was once his home turf comes with a twist: after being sent off in the first leg, he won’t be allowed on the sideline at the Bernabéu. And that stadium, with all its history and tension for the Portuguese coach, is central to the “curse” he’s hoping to break—one that has lingered for 24 years.

The one achievement Mourinho still doesn’t have

Mourinho is widely regarded as one of the greatest managers of all time. His résumé—trophies, iconic teams, unforgettable runs—speaks for itself. Yet there’s one milestone he has never reached: he has never beaten Real Madrid at the Bernabéu as a visiting coach.

And tonight, at around 3:00 p.m. ET, he gets another shot.

A 24‑Year storyline

Across his 25 years as a head coach, Mourinho has faced Real Madrid seven times. Tonight will be the eighth. Only two of those previous matchups took place at the Bernabéu.

His first visit came in the 2000–01 season—24 years ago—when he led a Porto side built around Deco. Madrid escaped with a late winner from Santiago Solari, leaving Porto empty‑handed in that Champions League group‑stage match.

The second and most recent time was also with Porto in the 2003–04 group stage. That year, Porto went on to win the Champions League—still the club’s most recent title. But before lifting the trophy, they had to navigate a group that included Real Madrid. In many ways, their Matchday 6 meeting in the Spanish capital was meaningless as both teams had already secured a place in the next round. The game ended 1–1 - Solari putting the hosts ahead on nine minutes and Derlei equalizing from the penalty spot on the half hour.

Tonight: a chance to rewrite the script

Now, Mourinho’s Benfica arrives in Madrid looking to overturn the tie and punch a ticket to the Round of 16. With his trademark ability to neutralize stronger opponents and his deep Champions League experience, the Portuguese coach has a real chance to make history—to win at the Bernabéu for the first time as a visiting manager. It would be another first as no Portuguese team has ever won at the White Coliseum in official competition.

If he pulls it off, it would be one of those classic Mourinho storylines: dramatic, improbable, and unforgettable.

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