Jose Mourinho will be a familiar face in the opposition dugout this week when Real Madrid conclude their league phase campaign in the Champions League.
Mourinho is now in charge of Portuguese giants Benfica, who host Los Blancos at Estadio da Luz on Wednesday, January 28.
There is little riding on the game, with Madrid virtually assured of passage directly to the Round of 16, while Benfica are languishing on six points and would need favours from elsewhere to reach the playoffs, even if they pull off an upset victory.
Still, it allows reminiscing over Mourinho's high-profile and polarising stint in charge of the 15-time European champions more than a decade ago – especially at a time of managerial flux at the Santiago Bernabeu, where plenty still hold the inimitable 63-year-old in high regard.
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When was Jose Mourinho coach at Real Madrid?
Jose Mourinho was Real Madrid head coach for three years after being appointed on May 28, 2010, after mounting speculation and the heavily symbolic factor of leading Inter Milan to Champions League glory at the Santiago Bernabeu.
That rounded off a historic treble for the Nerazzuri, who he also led to the Serie A title in 2008/09. Speaking after the 2-0 final win over Bayern Munich, Mourinho said he was "sad, as almost for sure it's my last game with Inter". He added: "If you don't coach Real Madrid then you will always have a gap in your career."
Madrid handed Mourinho a four-year contract. A key motivation behind his appointment was the former Porto and Chelsea boss being identified as the man to halt Pep Guardiola's Barcelona juggernaut.
Guardiola was an eyebrow-raising pick ahead of one-time Barca assistant Mourinho to succeed Frank Rijkaard at Camp Nou in 2008 before leading the Blaugrana to irresistible treble glory in 2008/09. He followed that up by retaining La Liga in 2009/10, despite Madrid and new signing Cristiano Ronaldo running up a 96-point season under Manuel Pellegrini.
The only man to notably check Barca's momentum that season was Mourinho when his Inter prevailed 3-2 on aggregate in the Champions League semifinals and he enjoyed a peacocking celebration on the Camp Nou turf.
When José Mourinho sprinted across the Camp Nou after Inter knocked Barcelona out of the Champions League before joining Real Madrid. 😉 pic.twitter.com/9nAStJGZD3
— Madrid Xtra (@MadridXtra) May 6, 2025
What did Jose Mourinho win at Real Madrid?
Mourinho's trophy haul at Madrid is fairly moderate given his and the club's reputations, as he lifted three honours in as many seasons.
Nevertheless, the fact that the two major ones came at the expense of Guardiola's Barcelona explains his enduring popularity among sections of Madridistas.
Ronaldo scored a stunning header to secure a 1-0 extra-time win over Barca in the 2011 Copa del Rey final. That game came in the middle of an unprecedented and tempestuous period of four Clasicos in 17 days. The teams drew 1-1 at the Bernabeu in La Liga, which Guardiola's side eventually won by a margin of 96 points to 92.
After Madrid's Copa triumph came a two-legged Champions League semifinal that was ultimately settled by a brilliant Lionel Messi brace in the Spanish capital. These four games, for better or worse, ultimately set the course for the rest of Mourinho's tenure with Los Blancos.
In 2011/12, Barcelona finally buckled and Madrid won La Liga with 100 points – nine better off than their bitter rivals – 121 goals, a +89 goal difference and 32 wins. All of those figures were La Liga records. In 2012, after Guardiola stepped away and handed the reins at Barcelona to Tito Villanova, Madrid won the Supercopa de Espana on away goals.
José Mourinho speaking openly about the El Classico, Messi and Cristiano and the match that gave Real Madrid the La Liga title at the Camp Nou. [Thread]
— IM🇵🇹 (@Iconic_Mourinho) June 24, 2023
Take the time of your life to watch this, it's worth it.Pic.twitter.com/6kaAzfSXfj
Did Mourinho win the Champions League at Real Madrid?
Mourinho did not win the Champions League with Madrid as the 2011 loss to Barcelona became the first of three consecutive semifinal reverses.
In 2012, Madrid lost on penalties to Bayern Munich at the Bernabeu, as Ronaldo, Kaka and Sergio Ramos erred from the spot after the two-legged tie finished all square at 3-3.
The following year, a Bundesliga giant once again dashed Mourinho's hopes. Jurgen Klopp's formidable Borussia Dortmund hammered Madrid 4-1 at Signal Iduna Park and a rally to win 2-0 in the return leg came too little, too late.
Which Real Madrid players did Mourinho not like?
The widely reported breakdown of relations between Mourinho and Madrid stalwarts Iker Casillas and Sergio Ramos was a key subplot of his final season.
After the atmosphere between Barcelona and Madrid players became incredibly fractious during the four Clasicos in 17 days, there was a need to mediate for the good of the Spain national team, which was itself in the middle of a historic run.
La Roja had won Euro 2008 and the 2010 World Cup and had a third successive tournament success in their sights at Euro 2012. A potential problem was the team being predominantly made up of Barcelona and Madrid players who had been at one another's throats. In the eventual 4-0 Euro 2012 final win over Italy, opening goalscorer David Silva was the only starter not to play for Madrid or Barca.
As key members of the Spain dressing room, goalkeeper Casillas and defender Ramos took it upon themselves to attempt mediation.
"I called Xavi and Puyol to bring an end to all of the anger between the Real Madrid and Barcelona players. We were creating a bad image, but I didn't ask forgiveness of anyone," Casillas told Canal+ in 2015. "Mourinho didn't talk to me about this call before it. I don't know if it bothered him, but people said that it did."
Ramos and Casillas purportedly mocked Mourinho's modest playing career, while Casillas' partner Sara Carbonero being a television reporter led to accusations of him leaking dressing room information, something the goalkeeper denies.
In hindsight, the breakdown in relations with influential senior players Ramos and Casillas marks a pivot point in Mourinho's career. Prior to Madrid, he was a man lionised by his players at Porto, Chelsea and Inter, with the likes of John Terry and Marco Materazzi seemingly ready to run through walls for their boss. After Madrid, there is a pattern across Mourinho's high-profile jobs and departures, most notably his return to Chelsea and at Manchester United, where he breaks ranks and lambasts players in public, figuratively setting everything on fire before walking away, unable to build the relationships of deep trust that underpinned his legacy-defining early career.
As the 2012/13 season slipped away from Mourinho and Barcelona ran away with La Liga despite Villanova being taken seriously ill, there were also reports of the coach's relationship with star man and compatriot Ronaldo being on the rocks. "Maybe thinks that he knows everything and that the coach cannot improve him anymore," Mourinho wondered aloud in May 2013.
Why did Jose Mourinho leave Real Madrid?
Ultimately, the bitter Barcelona rivalry that Mourinho did plenty to pour petrol on and the aforementioned breakdown of bonds in the dressing room were sustainable so long as Madrid were winning. By the end of 2012/13, things had become far too toxic.
Despite signing a contract extension through 2016 in the afterglow of Madrid's record-breaking 2011/12 La Liga win, president Florentino Perez announced Mourinho would leave Madrid by mutual agreement at the end of the season on May 20, 2013.
Mourinho confirming his departure came three days after a loss to rivals Atletico Madrid in the Copa del Rey final, prompting him to call the campaign "the worst of my career".
Speculation of either a return to Chelsea or a switch to Manchester United to succeed the departing Sir Alex Ferguson also swirlied. After the Champions League semifinal defeat to Dortmund, Mourinho told his post-match press conference: "I am loved by some clubs, especially one. In Spain it is different, some people hate me, many of you in this room."
After leaving Madrid, Mourinho returned to Chelsea for the 2013/14 season. He won the Premier League in 2014/15. It remains the most recent of Mourinho's eight top-flight titles, despite subsequent spells with Manchester United, Tottenham Hotspur, Roma and Fenerbahce. Benfica were third in the Primeira Liga heading into their European engagement with Madrid, sitting 10 points shy of leaders Porto, although Mourinho's side were unbeaten in 15 league games since his appointment.
What did Jose Mourinho say about Alvaro Arbeloa?
Alvaro Arbeloa will lead Madrid against Benfica, having taken over in the wake of Xabi Alonso earlier this month. In sharp contrast to the deterioration of his relationships with other members of the Santiago Bernabeu dressing room during his time in charge, Mourinho holds former Spain defender Arbeloa in the highest regard, saying he is like one of "my children".
Speaking at Tuesday's pre-match press conference, Mourinho spoke about Arbeloa while referencing his perceived criticism of Cristian Chivu, one of his former Inter players who is now in charge of the Nerazzuri.
"There is one problem – both Chivu and Arbeloa are my children, they are not just ex-players of mine, but they are special," he said.
"Speaking about Alvaro, I would say that he is one of the players – from a human point of view, from a personal point of view, and personal empathy – he is one of my favourites of them all.
"Obviously he is not the best player who has played for Real Madrid, but he is certainly one of the best men who has played for me at Real Madrid."
Arbeloa returned the compliment, saying – perhaps notably at a time of long-term managerial uncertainty at Madrid – "Jose will always be one of us."
Another chapter for Mourinho at Madrid? Well, they've gone back to both Zinedine Zidane and Carlo Ancelotti over the past decade. Stranger things have happened.