By a neat twist of fate, Jose Mourinho's first Champions League game of his new spell as Real Madrid manager sees Inter visit the Bernabeu on Tuesday evening. When first hired by Madrid at the end of 2009-10, Mourinho had just won a Champions League treble with Inter, and was widely viewed as the man most likely to end the Spanish giants' long wait for a 10th European Cup.

The following three turbulent years managing a team full of galacticos including Cristiano Ronaldo, Karim Benzema and Kaka brought semi-final heartbreak in the competition each season. Since Mourinho left in 2013, Madrid have won six Champions League trophies — three with Carlo Ancelotti as head coach (2014, 2022, 2024) and three under Zinedine Zidane (2016, 2017, 2018).

A decade of European disappointment

In that time, Mourinho has been involved in eight Champions League campaigns, including qualifying, with five different clubs. But you have to go back to the 2013-14 season for the last time he won a main-draw knockout tie. His Chelsea team made the semi-finals that campaign, only to be beaten by Atletico Madrid — thanks in no small part to the performance of Thibaut Courtois, then on loan at Atletico from the Stamford Bridge club.

In 2014-15, Mourinho's Chelsea featured Courtois, Eden Hazard, Cesc Fabregas and Diego Costa. They had the advantage in their last-16 matchup against Paris Saint-Germain when Zlatan Ibrahimovic was sent off early on in the second leg in London, but Laurent Blanc's team still edged possession over 120 minutes and progressed on away goals, with Mourinho facing heavy criticism for his management of the tie.

"It's embarrassing," said former Manchester United defender Gary Neville on Sky Sports. "(Chelsea) thought they were just going to walk through to the quarter-final. They're walking out."

The following season, Chelsea topped their Champions League group, but poor Premier League form saw Mourinho sacked in mid-December. His next Champions League participation came in 2017-18 with Manchester United. They progressed easily through the group stages, with five wins from six games. United were big favourites ahead of a last-16 meeting with Sevilla, despite coming into the tie amid turmoil, with Mourinho taking on big players he believed were underperforming.

Star midfielder Paul Pogba was dramatically replaced by a 21-year-old Scott McTominay for the first leg in Spain, which finished 0-0 mostly thanks to a string of saves by man of the match David de Gea. The return was also goalless until late on, with the Old Trafford crowd chanting "attack, attack, attack" in frustration at United's cautious tactics. Two late efforts from Sevilla's Wissam Ben Yedder put his team through as Romelu Lukaku grabbed a goal of little consolation.

Mourinho refused to take responsibility for that defeat, instead spending 12 minutes explaining United's lack of "football heritage" in his post-match press conference.

From Tottenham to Fenerbahce: A slow decline

Mourinho was fired by United in December 2018, returning to football almost a year later with Tottenham in November 2019 to replace Mauricio Pochettino, who had led Spurs to the previous season's Champions League final. A group-stage win over Olympiacos secured Tottenham's place in the last 16 that term, but an injury-hit team lost 4-0 over two legs to RB Leipzig in the round of 16.

For some time, it seemed that might turn out to be Mourinho's last stab at Champions League success. At Roma, his European role was in the lower-tier competitions, beating Feyenoord 1-0 in the 2021-22 Conference League final, then losing to Sevilla on penalties in the following season's Europa League decider.

During 2024-25, now at Turkish club Fenerbahce, Mourinho faced Rangers in the Europa League last 16. The build-up to that tie was dominated by a public row with another of his own team's players, this time French attacker Allan Saint-Maximin. After Rangers won on penalties following a 3-3 aggregate draw, Mourinho railed angrily against supposedly biased refereeing.

"For European finals, normally it depends on the club where you are," Mourinho said in a press conference after the defeat. Asked whether he still backed himself to win the biggest trophies, he annoyed many by saying even reaching a semi-final was an "impossible mission" for a Turkish club.

The following August, after a Champions League play-off defeat by Benfica, Mourinho was sacked by Fenerbahce. But incredibly, that failure actually paved the way for his return to the competition last season, with Benfica hiring him just weeks later.

The Benfica chapter and the road back to Madrid

Five defeats in their first seven league-phase outings meant Benfica had to beat Real Madrid in their final game and hope lots of results elsewhere went their way in late January. A dramatic night saw Benfica goalkeeper Anatoliy Trubin score an injury-time goal which amazingly sent his team through to the knockout rounds, where they again faced Madrid.

That knockout phase play-off brought more dramatic scenes. The first leg was stopped after Vinicius Junior said he had been racially abused by Benfica's Gianluca Prestianni, who denied the allegation. Prestianni was subsequently banned by UEFA and FIFA, having admitted to using a homophobic (rather than racist) slur against the Madrid forward. On that February 17 night, Mourinho suggested Vinicius Jr had incited the incident.

After that game, it was very difficult to imagine Mourinho's next Champions League opportunity coming with Madrid, who were the better team and progressed to the last 16 as 3-1 winners on aggregate. But at the end of last term, Madrid president Florentino Perez turned to him to shake up a side which had failed to win a major trophy for a second successive season.

The Ancelotti template

Mourinho is not the first veteran Champions League-winning coach whose career appeared on a downward slope before a surprise return to the Spanish capital. Ancelotti was appointed Madrid manager for a second time in June 2021, having just led Everton to 10th in the Premier League. He had not been involved in a Champions League knockout tie for four years. Inside 12 months of accepting Perez's call, Ancelotti was celebrating another Champions League trophy. Two seasons later, the Italian won the competition again — taking his personal tally of European Cups to five, more than any other manager.

Whether Mourinho can complete a similar late-career turnaround is now the big question at the Bernabeu. Ancelotti's genius during his second spell at Madrid was in how he understood his players and motivated them in the biggest games. He also leant into the club's fantastic history in the competition, especially during a series of remarkable comebacks on the way to success in 2021-22.

Those victories underlined Madrid's uniqueness in top-level football, especially under long-serving president Perez. The challenge for any Bernabeu coach is providing enough collective organisation within the team without cramping the style or the egos of his biggest individual stars. Mourinho surely knows this, both from personal experience first time round and having seen what has worked at Madrid during his time away — and also what did not work last season under first Xabi Alonso and then Alvaro Arbeloa.

A more mature Mourinho

Since returning in June, the Portuguese has been keen to project a much more relaxed personality and approach than during his previous spell in charge.

"I still have the same DNA," Mourinho told Spanish TV show El Chiringuito in the only media interview he has done since returning to Madrid. "Obviously, I can't hide who I am or try to be someone else. (But) I'm much more mature now, less emotional, more controlled."

Mourinho's aim to get closer to his players has been especially clear with the team's biggest names. He has warmly backed Vinicius Jr and encouraged Madrid's fans to support a player who they whistled last season. In that Chiringuito interview, he also addressed his comments about the Brazilian after that Benfica game — remarks that did not go down well with Vinicius Jr at the time, though sources close to the player later said he had no problem with Mourinho being appointed at Madrid. Last month, the 26-year-old forward extended his contract, despite strong interest from Arsenal.

"Prestianni was my player. That's it, there's no discussion," Mourinho said. "If Prestianni is my player... 20 players can come, I'm with Prestianni, there's nothing more to it. Vini knows that now, he knows which side I'm on and he knows that he can look at me and count on me to stand by him."

Jude Bellingham is thriving in an attacking midfield role that gives the Englishman lots of freedom. Kylian Mbappe has started the new La Liga season with four goals in four games. The defence has not looked quite as solid as their head coach would like, and they suffered a rather unlucky 1-0 defeat by Real Betis on Friday, but these are early days.

This 'new' Mourinho has not changed completely, however. He has also spoken about the need to refocus and remotivate a squad that has underperformed in the last two seasons. This fits with a narrative that many around the Bernabeu, including both Perez and Mourinho, have always maintained — that the winning mentality instilled at the club during his first term in charge was key to their Champions League successes after he left.

"I believe Mourinho's return is a great decision as he's a great winner and he knows the club," former Madrid stalwart Luka Modric, who is now at Milan and turns 41 on Wednesday, told Marca last week.

Whether the theory survives contact with reality remains to be seen, but few football fans will want to miss Mourinho's attempts to return to the Champions League's latter stages over the coming season.