Ranking Mourinho’s first signing at each club from best to worst: Real Madrid superstar to Tottenham stinker

Jose Mourinho is in line for a return to management with Benfica and attention will soon turn to which players he can lure to Portugal in the January transfer window.

Mourinho began his managerial career with Benfica in 2000, but didn’t last very long. It’s something the club have come to regret in the years since, throughout which he has won 26 major trophies. However, 25 years later, they’re on the verge of re-appointing him.

After leaving Fenerbahce recently, Mourinho hasn’t had to wait too long for his next job. While the calibre of club he has been in charge of has begun to decline in recent years, a manager of his stature has proven to be a huge benefit in attracting players.

Who will his first signing at Benfica be? That will only become clearer towards January, but will be the subject of some anticipation.

Until then, we’ve ranked the first signing he made at each of his previous clubs – not counting his first spell at Benfica, when he didn’t make any, or his time in charge of Uniao De Leiria – from best to worst.

Real Madrid – Angel Di Maria

Mourinho took charge of Real Madrid in May 2010, barely a week after completing the treble with Inter Milan.

Coincidentally, his first signing was from Benfica, but a player who played for the Portuguese side long after Mourinho himself had been there.

Angel Di Maria arrived from Benfica in June 2010 in a deal worth €25m plus €11m in bonuses.

The winger provided the assist for Cristiano Ronaldo’s winning goal against Barcelona in the Copa del Rey final, concluding his debut season with 26 assists and nine goals from 53 appearances in all competitions.

Under Mourinho’s guidance, Di Maria became a LaLiga winner in his second season in Spain.

The Argentina international outlasted Mourinho in Madrid by a year before his departure for a disappointing spell with Manchester United.

He ended his Real Madrid career with 85 assists and 36 goals from 190 appearances.

Chelsea – Paulo Ferreira

After working with Mourinho at Porto and winning the Champions League in 2004, Paulo Ferreira followed his compatriot to Chelsea at the start of his first reign there.

Costing just over £13m, the right-back featured heavily in his debut season as Mourinho led the Blues to the Premier League title at the first time of asking.

Ferreira stayed with Chelsea until his retirement in 2013, shortly before Mourinho’s return to the club for a second spell.

Although his gametime dwindled towards the end of his career, Ferreira left Chelsea with 217 appearances to his name and played a part in winning 12 trophies – half of which were with Mourinho.

At the peak of his powers, Mourinho labelled the dependable Ferreira as “the best right-back in the world.”

Porto – Maniche

Mourinho raided Benfica to sign Maniche for Porto in the summer of 2002, allowing him to take a functional role in his preferred position as a midfielder.

During his spell with Porto, Maniche won back-to-back Primeira Liga titles alongside UEFA Cup and Champions League glory.

He also went on to earn his full debut for Portugal at international level and was part of the squad that reached the final of Euro 2004, earning a place in the Team of the Tournament.

Mourinho later reunited with Maniche by taking him to Chelsea for a loan spell in 2006, but it wasn’t a success.

Roma – Rui Patricio

Roma’s appointment of Mourinho in May 2021 came out of the blue and initially generated a wave of enthusiasm in the Italian capital.

A primary issue they had to address in their squad at the time was the goalkeeping position, which had been a problem for three years since their sale of Alisson Becker to Liverpool.

Mourinho used his Portuguese connections – and relationship with shared agent Jorge Mendes – to bring in Rui Patricio from Wolves.

Patricio enjoyed a successful first season, winning the Europa Conference League as a member of the Team of the Season.

However, as had happened towards the end of his time with Wolves, Patricio’s form declined and he was dropped by Mourinho for his final game in charge of Roma in January 2024.

Manchester United – Eric Bailly

Yet another shockwave-inducing appointment in his storied career, Mourinho’s move to Manchester United in 2016 was a huge talking point in the Premier League.

His first signing was Eric Bailly, who joined from Villarreal in a deal worth £30m.

Bailly’s United career began with man-of-the-match performances in the Community Shield and on his Premier League debut.

By the end of the season, Bailly helped United to the Europa League title, acknowledged as a member of the Squad of the Season.

However, the 38 appearances he made in all competitions in 2016-17 were the most he would ever manage in any of his six full seasons with United, as injury issues proved to be brutal.

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Chelsea – Andre Schurrle

Just 10 days after Mourinho’s return to Chelsea in 2013 was announced, the Blues reached an agreement for his first reinforcement: Andre Schurrle.

The German forward had been plying his trade for Bayer Leverkusen before Chelsea gave him his first chance of moving outside his native country.

Schurrle lasted 18 months at Chelsea and endured mixed fortunes, scoring 14 goals before returning to the Bundesliga with Wolfsburg in search of more playing time.

Despite that, Schurrle had featured enough over the first half of the 2014-15 season to be eligible for a Premier League winner’s medal, which Mourinho was glad to inform him of.

Inter Milan – Mancini

One of Inter’s first orders of business after appointing Mourinho in 2008 was to keep Hernan Crespo on a permanent basis after his loan spell from – and then release by – Chelsea, where the Special One had already worked with him.

Inter’s first outright new signing for Mourinho was someone else with Serie A experience, as the Brazilian winger Mancini arrived after a five-year spell with Roma.

Mancini had scored 59 goals for Roma, but only managed two for Inter, from a total of 36 appearances.

Inter even loaned him to their rivals AC Milan in 2010, before eventually getting rid for good in January 2011 thanks to Atletico Mineiro taking him back to Brazil.

Fenerbahce – Levent Mercan

Mourinho took on the Fenerbahce job in June 2024 and went on to attract some familiar faces such as Allan Saint-Maximin, Sofyan Amrabat and Youssef En-Nesyri to the Turkish Super Lig.

But Fenerbahce’s first signing after the appointment of Mourinho was Levent Mercan from fellow Turkish side, Fatih Karagumruk.

The left-back struggled to win Mourinho over, though; only played in 11 league games during the 2024-25 season and was left out of their Europa League squad.

Mercan didn’t seem to take it personally, explaining in March 2025:  “Mourinho is an incredible figure both for his football knowledge and as a person. There’s a reason they call him ‘The Special One.’ I mean this in a completely positive way—his approach to players is truly unique. Working with him and fulfilling his demands is a big motivation for me.”

Tottenham Hotspur – Gedson Fernandes

There were high hopes for Fernandes when Tottenham brought him to the Premier League as a 21-year-old in January 2020. Within their agreement for an 18-month loan move was an option to buy for a reported fee of €50m.

But it soon transpired a permanent deal was never going to be realistic. Fernandes never started a Premier League game and saw his loan terminated six months early.

“These six months become really, really bad for us and for him,” Mourinho conceded in December 2020, shortly before his recall.

“On top of it he’s a kid, it’s incredible what I’m going to say, but since he arrived he didn’t miss one single minute of one training session so even in low levels of happiness and motivation he is managing to be a very good professional.

“So hopefully better days will come for him and they will come for sure, with us or without us, but better days will come for sure.”

Fernandes has since played in Turkey for three different clubs before moving to Russia with Spartak Moscow in July 2025.