José Mourinho has never been afraid to revisit an old ground. Across a career built on intensity, trophies, and spectacular falling-outs, he has returned to Benfica, Chelsea, and now Real Madrid. The record, as ever, is more complicated than the man himself would have it.
Benfica: The first step (2000) and an unbeaten return (2025-26)
Mourinho’s very first senior management job was at Benfica, where he succeeded Jupp Heynckes in 2000. It lasted just 11 games (six wins, three draws, two defeats, and no trophies), before he resigned over a disagreement with the club’s new ownership structure.
Twenty-five years later he returned, hired in September 2025 in the most ironic of circumstances: Benfica had just knocked his Fenerbahçe side out of the Champions League qualifying round, and the Lisbon club promptly appointed him as their new manager.
Mourinho went unbeaten in the Primeira Liga during his second spell, but again left without a domestic or European title. However, the Champions League campaign produced a moment that will live in Benfica’s memory: a 4-2 win over Real Madrid in the league phase, with a 97th-minute header by goalkeeper Anatoliy Trubin’s.
Chelsea first spell (2004-2007): The template
Mourinho arrived from Porto in June 2004 having just won the Champions League, immediately declared himself “a Special One” at his first press conference, and proceeded to deliver Chelsea’s first league title in 50 years in his debut season (with a record 95 points and 15 goals conceded – a Premier League defensive record that still stands).
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A native from Setúbal, Mourinho retained the title the following season and added an FA Cup, a Community Shield and two League Cups across his three years at the club, departing in September 2007 “by mutual consent” after reported disagreements with owner Roman Abramovich, according to the BBC.
Across those years, Chelsea reached the Champions League semi-finals twice.
Real Madrid first spell (2010-2013): Records broken, Europe elusive
Mourinho was appointed at the Bernabéu in the summer of 2010, tasked with ending Pep Guardiola’s Barcelona’s stranglehold on Spanish football and European competition. The Portuguese manager won three trophies in three seasons: Copa del Rey in 2011 (Real Madrid’s first cup in 18 years), La Liga title in 2012, and the Spanish Super Cup in 2013.
Yet the Champions League eluded him all three seasons. Madrid fell at the semi-final stage every year: to Barcelona in 2011, to Bayern Munich on penalties in 2012, and to Borussia Dortmund in 2013. The third exit proved fatal. “This is the worst season of my life,” Mourinho told the press afterwards.
The dressing room had fractured. Reports circulated of rifts with Iker Casillas, Cristiano Ronaldo, and Sergio Ramos. Two days after the Champions League elimination, Florentino Pérez announced the “mutual” end of the relationship, though Mourinho himself has consistently maintained that he left on his own terms.
“I must be one of the few Real Madrid coaches to leave without being sacked,” he told the press ahead of Benfica’s Champions League tie against Madrid earlier in 2026. “When you leave of your own accord, you have nothing to envy. I left with a clear conscience,” said the former Benfica coach.
🚨👀 José Mourinho: “I am one of the few coaches who left Real Madrid without being sacked”.
“The day I left, the president told me: you have done the difficult thing, now comes the easy”.
“All the Champions Leagues afterwards brought me happiness”. 🏆😁 pic.twitter.com/64zKud9DRW
— Fabrizio Romano (@FabrizioRomano) February 16, 2026
Chelsea second spell (2013-2015): Sweet and sour
Mourinho returned to Stamford Bridge in June 2013 “nine years and a day” after his first appointment. The first season produced nothing (a third-place finish and a Champions League semi-final exit). The second season delivered a League Cup in March 2015 and the Premier League title in May, Chelsea’s first since his departure.
What followed was historically abrupt. Mourinho signed a new four-year contract in August 2015, but by December he was gone. Mourinho was relieved of his duties after Chelsea lost nine of their first 16 league games and sat one point above the relegation zone.
The return: “I want the best players”
Mourinho was confirmed as Real Madrid’s new coach ahead of the 2026-27 season, returning to the club he has repeatedly identified as the ultimate reference point in world football. In an interview on the Beast Mode On podcast (video below) with Adebayo Akinfenwa, José Mourinho dismissed suggestions he would use his return to clear out players involved in last season’s dressing room controversies.
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“I’ve read some things saying that Jose is coming here and he’s going to cut some of the best players who supposedly had problems during the season. No, no, I want these players, I want the best,” he said. “Now I have to find a way to have a team and not have the problems that, I don’t know, from what I’ve read, they had in previous seasons.”
Asked about his Madrid players’ involvement in the World Cup, he joked: “You want the truth? I want the Real Madrid players to lose and go on vacation. Because I want them back for pre-season.”
