José Mourinho's Career: Finals, Triumphs, and the One He Regrets
José Mourinho has managed more finals than most coaches dare to dream of. Yet when he looks back over a 26-year career on the touchline, one night still gnaws at him.
Not the ones he won. The one that got away.
The final he wants back
Asked on the Beast Mode On Podcast to name a single match he would replay if he could, the answer came without hesitation.
“Roma - Sevilla, Europa League final. Without Anthony Taylor!”
No filters. No softening with time.
That night in Budapest, Mourinho’s Roma were edged out by Sevilla on penalties, his first defeat in a European final. The game burned with tension from the first whistle to the last kick, and even beyond it. Mourinho clashed furiously with the Premier League-based officiating team, led by referee Anthony Taylor, and the fallout rumbled on long after the trophy had been lifted.
Everyone has moved on professionally. Careers have twisted in different directions. But the emotions clearly have not cooled. Not for him.
A Roman chapter that changed a city
Mourinho’s spell at Roma was chaotic, combustible, and unforgettable. It was also historic.
He dragged the Giallorossi to back-to-back European finals and delivered something no one else had ever done: the full UEFA treble. Champions League, UEFA Cup/Europa League, and then the newly born Conference League. Three different competitions, one manager at the centre of all of them.
Roma’s triumph over Feyenoord in the 2022 Conference League final did more than fill a space in the club museum. It ended an 11-year wait for major silverware in the Italian capital and lit a fuse under an already volatile football city.
“When we won the Conference League in Roma, that city went mad,” Mourinho recalled. You can picture it as he speaks: the streets flooded, the horns, the flares, the songs that don’t stop.
“I believe that we did to that city what Champions League winners cannot do in other cities. Roma is a city where people are really, really, really in love with that club. A giant club with incredible passion. Absolutely incredible.”
He’s won league titles in Portugal, England, Italy and Spain. He’s lifted the Champions League with Porto and Inter. Yet when pressed on the achievement that makes him most proud, his mind goes back to that first season in Rome and to a competition many initially dismissed.
“Of course, when we won the Conference League it was the first season of the Conference League, I don't think Europe was giving [recognition] to the Conference League what it is giving now. When we arrived in Rome and we went for the parade around the Colosseum, Circus Maximus, you realise what you gave to those people.”
The image is vivid: the bus crawling past the Colosseum, sweeping toward Circus Maximus, a sea of Roma shirts surging around it. A coach who has seen almost everything in football, suddenly aware he has tapped into something deeper than a line on his CV.
Anfield, dressing rooms and a second Bernabéu act
Mourinho has never shied away from naming the toughest arenas and the biggest stages. Asked for the most intimidating away ground he has faced, he did not reach for diplomacy.
He went straight to Anfield.
Liverpool’s home, with its snarling noise and suffocating intensity on European nights, left the deepest mark on him as an away coach.
At the other end of the spectrum, he points to Real Madrid when talking about the best dressing room environment. It is a room he knows well and one he is about to walk back into. With a three-year contract signed, he returns to the Santiago Bernabéu for a second spell, this time inheriting a squad stacked with star power: Jude Bellingham, Kylian Mbappé, Vinícius Júnior and more.
During his first reign in Madrid between 2010 and 2013, he prised La Liga and the Copa del Rey out of Barcelona’s grip. It was a period defined by ferocious rivalry and relentless scrutiny, yet it still delivered major trophies and enduring memories.
Now he comes back to a club that has barely stopped winning in his absence, yet still demands more. That is the paradox of Real Madrid. Even success feels like a starting point.
Mourinho, as ever, is not returning to make up the numbers. He wants to put Madrid “back on the trophy trail”, even if the club never truly left it. A domestic title here, a cup there, another deep run in Europe – that is the expectation, not the ambition.
The man who once turned Rome upside down with the Conference League now steps back into a city where parades are measured in Champions Leagues. The question is not whether he can ignite passion. It is whether, in this second act at the Bernabéu, he can write something that even he will rank alongside Rome, Porto, Milan – and perhaps, one day, erase the sting of that night against Sevilla.
