José Mourinho Reflects on His Most Painful Match

José Mourinho has coached in some of football’s most fevered arenas, lifted the game’s biggest prizes and survived its fiercest storms. Yet when he looks back over 26 years in the dugout, one night still burns.

Not a victory. A wound.

The one game he’d play again

Asked on the Beast Mode On podcast to choose a single match he would replay, Mourinho didn’t hesitate.

“Roma - Sevilla, Europa League final. Without Anthony Taylor!”

The 2023 Europa League final in Budapest still lives under his skin. Roma, chasing a second straight European trophy under the Portuguese, dragged Sevilla into a street fight of a final that eventually slipped away on penalties. It was Mourinho’s first defeat in a European showpiece, and the night ended with him raging at the English refereeing team in the bowels of the stadium.

Everyone else has moved on. Sevilla lifted the trophy. Anthony Taylor went back to the Premier League. Roma changed coach. Yet as Mourinho circles back to Real Madrid for a second spell at the Santiago Bernabéu, that night continues to stalk him.

The trophies, the comebacks, the touchline sprints – all of them sit behind a single regret. If he could rewrite one chapter, it would be that one. Same teams. Same stakes. Different referee.

Roma, a city that “went mad”

The irony is that his time in Rome also delivered one of the most emotional triumphs of his career.

During an intense stint with the Giallorossi, Mourinho dragged Roma to back-to-back European finals. In 2022, they beat Feyenoord in the inaugural Europa Conference League final, ending the club’s 11-year wait for a major trophy and making Mourinho the first coach to complete UEFA’s full set: Champions League, UEFA Cup/Europa League and Conference League.

He has won league titles and cups in Portugal, England, Italy and Spain. He has lifted the Champions League with Porto and Inter. Yet when asked which achievement makes him most proud, he went straight back to that night with Roma.

“I did a few! When we won the Conference League in Roma, that city went mad.

“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.

“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.”

You can picture it: the bus crawling past the Colosseum, flares cutting through the night, a city that has seen empires rise and fall losing its composure over a trophy many had mocked. For Mourinho, who feeds off feeling as much as silverware, that mattered.

Anfield, Bernabéu and the roads he knows best

Mourinho’s career has taken him to almost every intimidating arena in the sport. Asked to name the toughest away ground he has faced, he didn’t dress it up.

Anfield.

The home of Liverpool, with its snarling noise and tight, heaving stands, sits at the top of his list. This from a man who has walked into Camp Nou, the Allianz Arena and San Siro with everything on the line.

If Anfield is the most hostile, the best dressing room, in his eyes, belongs to Real Madrid. And he is about to walk back into it.

He has signed a three-year deal with Los Blancos, returning to a club where he previously delivered La Liga and Copa del Rey titles between 2010 and 2013. That first spell was defined by ferocious battles with Barcelona and a relentless domestic points machine. This time, he inherits a squad loaded with star power and expectation.

• Jude Bellingham.
• Kylian Mbappé.
• Vinícius Júnior.

Names that define the modern game, all sharing a space Mourinho considers the finest environment he has worked in.

Back to Madrid, back to the hunt

The mission is clear. Madrid expect trophies, not stories. Mourinho, who once made a habit of turning clubs into serial winners, is being asked to do it again.

He has already proven he can bend a club’s identity to his will in the Spanish capital. That 2011–12 La Liga title, won with a record points haul, still stands as a reference point for intensity and ruthlessness. The Copa del Rey triumph, prising the cup away from Barcelona, remains another sharp memory.

Now, as he prepares for a second act at the Bernabéu, he does so with two powerful images in the rear-view mirror: a city of Rome losing itself in joy around the Colosseum, and a night in Budapest he would give anything to play again.

One showed him what he could still give a club.

The other reminds him what he still wants to take back.