José Mourinho was never going to fade away quietly. That reality will feel like a recurring nightmare for Real Madrid as they prepare to face Benfica with their UEFA Champions League ambitions on the line.

Having turned the “Special One” into the “Normal One” during three fractious years at the Bernabéu between 2010-13, Madrid know enough about Mourinho to expect a sting in the tail when they compete with his Benfica team for a place in the round of 16 over the next eight days.

Mourinho has already returned to haunt his former club this season by overseeing last month’s incredible 4-2 league-phase victory for Benfica — sealed by goalkeeper Anatoliy Trubin‘s memorable headed goal in stoppage time — which dragged Madrid into the playoffs and kept the Lisbon team in the competition. The two clubs were then paired together to meet again on Tuesday at Estadio da Luz ahead of next Wednesday’s second leg in Madrid.

– Everything you need to know about the UCL knockout rounds
– Coaching chaos: Get ready for 2026 manager merry-go-round
– Ranked: The top 25 manager jobs in soccer, from best to worst

But with Mourinho tipped to succeed Roberto Martínez as Portugal coach following the 2026 FIFA World Cup, every Champions League tie could now be the 63-year-old’s last. And this matchup could not be a more fitting occasion for Mourinho to delay his Champions League farewell — a game in the competition that made him against the club that broke him.

Is Mourinho the type of personality who would take great satisfaction from taking revenge against Madrid, 13 years after leaving the Bernabéu, by knocking them out of the Champions League? Absolutely.

It’s true that, since his three years as Madrid coach came to an end in 2013, after winning just one LaLiga, Copa del Rey and Supercopa, Mourinho has won more major honors than most coaches. But he has always been the type to measure himself against the best rather than the rest.

He won a Premier League title with Chelsea in 2015, the UEFA Europa League with Manchester United two years later — he also won League Cups while at Stamford Bridge and Old Trafford — and the UEFA Conference League with AS Roma in 2022. But the really big stuff on Mourinho’s CV came before he walked into the Bernabéu and engaged in the dual battle of managing a skeptical dressing room at the same time as taking on Pep Guardiola’s Lionel Messi-inspired Barcelona team.

Before he took charge of Madrid, Mourinho was a serial winner — Champions League titles with FC Porto and Inter Milan (the later as part of a treble), domestic cups galore in Portugal, England and Italy, and six league titles in eight years with Porto, Chelsea and Inter.

He amassed 17 trophies in those eight years, but just nine in the 16 years since with Madrid, Chelsea (again), United, Tottenham Hotspur, Roma and Fenerbahce. The rot set in at Madrid.

At the Bernabéu, there were bust-ups with powerful and influential senior players including Iker Casillas and Sergio Ramos, and he also lost his air of invincibility during a bruising rivalry with Guardiola. Having previously commanded a sense of undying loyalty from big players at Porto, Chelsea and Inter, Mourinho lost that connection at Madrid and it never returned, with similar clashes with star players — Eden Hazard (Chelsea), Paul Pogba (Man United), Dele Alli (Spurs) — during subsequent managerial roles at other clubs.

play

Did José Mourinho get lucky with Benfica’s playoff qualification?

Gab Marcotti and Julien Laurens break down the dramatic finish to Benfica’s clash with Real Madrid, where goalkeeper Anatoly Trubin stunned everyone by scoring a last-minute header to send Benfica through to the Champions League playoffs.

Sources who worked with Mourinho during his two spells at Chelsea say he was a changed character in his second period in charge. His time at Real Madrid left permanent scars and made him a more abrasive, unpopular character in both the dressing room and the boardroom. Mourinho has also been unable to revive his record as a winner of the biggest trophies, despite working for some elite clubs and, as a consequence, his jobs have become less attractive with each spin on the managerial merry-go-round.

Publicly, Mourinho has said that his time at Madrid was a high point. He told Portugal’s Channel 11 in 2019: “Real Madrid was my best experience because of what I learned as a coach, as a man, from the lessons I took in my career and in my life. It’s the best memory of my career, it was fantastic.” But the reality suggests something different.

It was the biggest job of Mourinho’s career, but it ended with a lack of fulfillment and the levels of success expected by him and Real, his time at the Bernabéu will always carry an air of “what might have been.”

But no matter where he has been, Mourinho has never lost the ability write his own headlines, and the 4-2 win against Madrid last month was classic Mourinho. Had he not ordered his goalkeeper Trubin to go forward in a final roll of the dice, Benfica would have failed to score the crucial goal to take them into the playoff round, and there would be no doubleheader with Madrid to look forward to this week.

Mourinho has not coached a team at the Bernabéu since leaving in 2013 — he guided Inter to Champions League glory against Bayern Munich at the stadium in the 2010 final — so his return to Madrid for the second leg next week will evoke all kinds of emotions, both for Mourinho and the home supporters.

So there is every reason for Real Madrid to be wary about their reunion with Mourinho. He might just have one last moment in the Champions League spotlight.