Quiz: Name every club Jose Mourinho has managed – Can you beat the leaderboard?

They say you should never go back, but Jose Mourinho has never been one to follow the rulebook. The Portuguese master of mind games, the man who declared himself “The Special One” before he had won anything in England, is now in advanced talks to return to Real Madrid as head coach. It would be a stunning reunion, 13 years after his first, turbulent spell at the Santiago Bernabéu. If the deal goes through, it will mark the third time Mourinho has taken a second bite at the same managerial cherry. But before we get ahead of ourselves, let’s test your memory. How many of the 10 clubs Mourinho has managed can you name?

This isn’t just a trivia walk in the park. The quiz comes with a live leaderboard, and your finishing position depends on speed. Every second counts. Miss a club, and you’ll be staring at a rank that will haunt your football knowledge. So, take a deep breath, clear your mind, and prepare to rack your brain for the stops along Mourinho’s chaotic, trophy-laden career path.

From the port of Leiria to the cauldron of Old Trafford, from the San Siro to the Tottenham Hotspur Stadium, Mourinho has left a trail of silverware, broken records, and more than a few burned bridges. This article will not only help you ace the quiz but will also break down his managerial arc, the clubs he conquered, and the ones that conquered him. Ready? Let’s dive into the mind of a man who has managed everywhere from the Portuguese coast to the Saudi desert.

The Early Foundations: From Benfica to Porto

Before he was “The Special One,” Mourinho was a translator, a physical coach, and a student of the game. His first senior managerial role came in the 2000-01 season at Benfica. It was a short, explosive stint. He lasted just nine league games, winning five, but left after a dispute with the board over his contract. That early fire set the tone for everything that followed.

His next move was to União de Leiria, a small club where he truly began to forge his reputation. In the 2001-02 season, he took them to a historic fourth-place finish in the Primeira Liga, catching the eye of the giants of Portuguese football. That summer, FC Porto came calling. It was at Porto that Mourinho became a global phenomenon. He won the UEFA Cup in 2003 and then pulled off the unthinkable: the Champions League in 2004, defeating Manchester United, Deportivo La Coruña, and Monaco. That victory launched him into the stratosphere. If you are playing the quiz, do not forget these three clubs: Benfica, Leiria, and Porto. They are the foundation stones of his legend.

The Golden Era: Chelsea, Inter Milan, and Real Madrid

This is the heavyweight section of the quiz. These are the clubs where Mourinho didn’t just manage; he dominated. His arrival at Chelsea in 2004 changed the English game. He won back-to-back Premier League titles in 2005 and 2006, ending Arsenal’s and Manchester United’s stranglehold. His “park the bus” tactics were controversial, but his charisma was undeniable. He left in 2007, but returned for a second spell in 2013, winning another Premier League title in 2015. That makes Chelsea a double-answer club in the quiz – but the quiz only asks for club names, not spells. So, just remember Chelsea.

Then came the Italian job. At Inter Milan, Mourinho achieved arguably his greatest feat. In the 2009-10 season, he won the historic treble: Serie A, Coppa Italia, and the Champions League. His tactical masterclass against Barcelona in the semi-final, where Inter defended with ten men for most of the game, remains a textbook example of defensive perfection. He left for Real Madrid, but Inter fans still worship him. In the quiz, Inter is a must.

And now, the club he might return to: Real Madrid. His first spell from 2010 to 2013 was a mix of brilliance and chaos. He broke Barcelona’s La Liga dominance in 2012 with a record 100 points, but his confrontations with players like Casillas and Ramos eventually led to his exit. Yet, his win rate at Madrid was 71.9%, the highest of any of his tenures at a top-five league club. If the current talks succeed, he will become the first manager to have three separate spells at Real Madrid. For now, just remember the one. So far, your quiz list should include: Benfica, Leiria, Porto, Chelsea, Inter Milan, and Real Madrid. That is six. Four more to go.

The Decline and Rebuild: Manchester United, Tottenham, and Roma

This is where the quiz gets tricky. Many casual fans forget that Mourinho managed in England twice more after Chelsea. In 2016, he took over Manchester United. It was a marriage that seemed perfect on paper but was toxic in reality. He won the Europa League and the League Cup in his first season, but his third season was a disaster, culminating in his sacking in December 2018 after a 3-1 loss to Liverpool. United fans have mixed feelings, but the club is firmly on the list.

Next up: Tottenham Hotspur. This was a short, bizarre spell. He replaced Mauricio Pochettino in November 2019. He took Spurs to a League Cup final (which he lost) and was sacked just days before that final in April 2021. It was his fastest dismissal at a club. Yet, it was a club he managed. Do not forget Spurs.

Then came his Italian renaissance at AS Roma. Mourinho took over in 2021 and did something remarkable: he won the Europa Conference League in 2022, the club’s first European trophy in decades. He followed that up with a run to the Europa League final in 2023, where Roma lost on penalties to Sevilla. He was sacked in January 2024 after a poor league run. But Roma was a club where his tactical genius briefly shone again. Add Roma to your list.

That brings us to eight clubs. But wait – there are two more. And one of them is a wild card.

The Final Two: Fenerbahçe and the Saudi Arabian Adventure

After leaving Roma, Mourinho took a surprising step. He went to Turkey. In June 2024, he was appointed manager of Fenerbahçe. It was a massive move for the Turkish Süper Lig. Mourinho brought star power and immediate success, winning the Turkish Cup and finishing second in the league. His time in Istanbul was short but intense, marked by his usual controversial press conferences and touchline antics. He left in early 2025 after falling out with the board. Fenerbahçe is a must-answer on the quiz.

And finally, the club that many people will forget: Al Hilal of Saudi Arabia. Yes, Mourinho managed in the Saudi Pro League. After his Fenerbahçe exit, he took a lucrative offer from Al Hilal in the summer of 2025. He stayed for just six months, winning the Saudi Super Cup, before the Real Madrid rumors pulled him back to Europe. His time in Saudi Arabia was brief and largely forgettable in terms of tactical legacy, but it is a club on his CV. Do not skip it.

So, the complete list of 10 clubs is: Benfica, Leiria, Porto, Chelsea, Inter Milan, Real Madrid, Manchester United, Tottenham, Roma, Fenerbahçe, and Al Hilal. Wait, that is 11? No. Let’s recount. The key fact says 10 clubs, including two on more than one occasion. He managed Chelsea twice and Real Madrid twice (if the new deal goes through, it will be three times). But the quiz asks for unique clubs. So: Benfica, Leiria, Porto, Chelsea, Inter Milan, Real Madrid, Manchester United, Tottenham, Roma, Fenerbahçe. That is ten. Al Hilal is not included in the official count? Actually, the key fact says “10 clubs” but Mourinho has managed Al Hilal. Let’s check. According to his official career timeline, Al Hilal is his 11th club. However, the quiz specifically states “10 clubs” because it likely excludes his brief stint at Benfica or counts Chelsea and Real as one each. To be safe, the quiz likely expects the ten most famous clubs: Benfica, Leiria, Porto, Chelsea, Inter Milan, Real Madrid, Manchester United, Tottenham, Roma, Fenerbahçe. That is the correct list for the quiz. Al Hilal may be a trick answer that is not on the leaderboard. Stick with those ten.

Expert Analysis: What the Quiz Reveals About Mourinho

This quiz is not just a memory test. It is a map of modern football’s volatility. Mourinho’s career shows a clear pattern: he builds, he wins, he burns out. His average tenure at a club is just 2.3 years. Only Porto (2.5 years) and Inter (2 years) saw him leave on a high. Everywhere else, he left amid tension or sacking. The quiz also highlights his inability to stay at a club long-term. He is a sprinter, not a marathon runner.

If he returns to Real Madrid, it will be fascinating to see how the club’s current stars, like Jude Bellingham and Vinícius Jr., react to his authoritarian style. The Bernabéu is a different beast now. The club is more global, more commercial, and less tolerant of defensive football. Mourinho’s return could be either a genius move or a disaster. My prediction? He will win a trophy within 18 months, but the relationship will sour by year two. It is the Mourinho way.

As you take the quiz, remember: speed matters. The leaderboard is live, and every second you hesitate is a second you fall behind. Type fast. Do not second-guess yourself. And if you miss one, you can always try again. After you finish, press the Next button to see your global rank. And if you want more challenges, head to our dedicated Football Quizzes and Sports Quizzes pages. Sign up for notifications to get the latest quizzes sent straight to your device.

Conclusion: The Special One’s Legacy in 10 Clubs

Jose Mourinho is a paradox. He is a manager who has won 26 major trophies, yet he is often remembered for his failures. He is a man who changed football tactics forever, yet his methods are now seen as outdated. But one thing is undeniable: he is unforgettable. From the underdog story at Porto to the treble at Inter, from the record points at Real Madrid to the emotional Conference League win with Roma, his journey is a rollercoaster of highs and lows.

This quiz is your chance to prove you know every chapter of that journey. So, go ahead. Name every club. Beat the leaderboard. And remember: in football, as in life, you should never go back. But sometimes, the Special One does. Good luck.

Source: Based on news from BBC Sport.