Ranking every stint of Jose Mourinho’s career from worst to best: Man Utd, Chelsea, Real Madrid…

The game might have moved on from him somewhat, but Jose Mourinho will undoubtedly go down as one of the greatest modern football managers of all time.

A revolutionary in his young career, Mourinho arrived at the top of the game having already done the unthinkable with Porto, then went one further and shook the Premier League to its core by putting Sir Alex Ferguson and Arsene Wenger up against the fences of the retirement home in the 2000s.

Along with a glut of domestic and European honours is a character like no other. A combination of arrogance, charm and wit, there really is nobody like Don Jose in today’s game. Whether or not that is a good or a bad thing is for you to decide.

In honour of the ‘Special One’ who was most recently relieved of his duties at Roma, we’ve ranked all 10 of his stints as a manager to date from worst to best.

10. Tottenham

Mourinho fans, we must collectively agree from this point forward to never acknowledge his torrid spell at Spurs.

Seriously, what was that about? Appointed to replace Mauricio Pochettino in 2019, it felt like the wrong move from the off. Highlights included Harry Kane at the peak of his powers, the Amazon docu-series and leading Spurs to the League Cup final in 2021 – the entire reason he was appointed – only to be sacked literally days before it.

Oh, and of course lots of horrid football.

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9. Benfica

His first gig as a manager in the professional game, a young Mourinho took the top job at Benfica in September 2000, replacing none other than Jupp Heynckes.

It was short, sweet and the most Mourinho thing you could imagine. After a short flurry of success and a shock in the presidential elections at the club, Mourinho used a win over Sporting CP in December as leverage to ask for an improved contract.

New club president Manuel Villarinho – who intended to eventually replace him with club legend Toni – refused, and Mourinho resigned after nine games in charge.

8. Uniao de Leiria

After his spell at Benfica, Mourinho stayed in Portugal and was able to stay in management, rather than dropping back down to assistant management, taking charge at Uniao de Leiria in July 2001.

His time in Leiria was again short, but very sweet. By January 2002, he had been poached for the job at Porto. It’s hard to rank this stint any higher, merely due to the short amount of time he spent at the club.

7. Manchester United

Mourinho has been on the record in saying that finishing second in the Premier League with United in 2017-18 was the biggest achievement of his career, but if you look between the lines, that’s simply one of the many ways he cleverly masks his shortcomings.

Taking charge at Old Trafford in 2016, it all started brilliantly. Paul Pogba and Zlatan Ibrahimovic were firing as his side won the Europa League and Carabao Cup, but that’s where it all peaked.

The press conferences were brilliant, but the football was far from it. By 2018-19, those pressers and iconic Bond villain moments had grown tiresome and he was sacked having failed to progress United or win a league title, while spending an obscene amount of money and alienating a then-in-form Anthony Martial among several other players.

6. Roma

There are plenty of parallels between Mourinho’s spells at United and Roma.

A strong start and a European trophy in season one quickly descended into chaos and Mourinho was unable to live up to – perhaps lofty – expectations from the powers above, resulting in torrid football and blockbuster media moments as he went into business for himself.

See also – lots of red cards.

Ranks marginally higher than United, though, purely based on expectations being a touch lower and him delivering their first-ever European trophy.

5. Chelsea (2013-15)

Mourinho’s second spell at Stamford Bridge perhaps best sums up his managerial career. Romance, implosion and everything in between.

He brought back Didier Drogba to win another Premier League in 2014-15 after a low-key return in 2013-14, then left in December 2015 with Chelsea a point above the relegation zone at Christmas, braced for another interim spell with Guus Hiddink after possibly the worst title defence of all time.

Football heritage.

4. Real Madrid

Competing with Pep Guardiola and perhaps the greatest club side football will ever see, Mourinho faced an uphill battle during his time in charge of Real Madrid from 2010 to 2013.

The fact he was able to steal La Liga away from Barcelona in 2011-12 in record-breaking fashion is probably a bigger achievement than anyone gives him credit for, even if we do sound like we’ve been listening to Mourinho himself too much in claiming that.

It fell apart in 2012-13 – inevitably – but at their best, Jose’s Madrid were one of the most joyous sides we’ve seen in recent times. They won La Liga with record games won (32), most away wins (19), 100 points and a record 121 goals scored.

He also took them forward in Europe, taking them to three successive Champions League semi-finals after years of chronic underachievement. You can certainly make the case those years were important groundwork for going on to lift the trophy, time and again, under successors Carlo Ancelotti and Zinedine Zidane.

A La Liga, Copa Del Rey and Spanish Supercup doesn’t do this tenure justice. 

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3. Porto

The reign that started it all. With Porto struggling in January 2002, they poached Mourinho from Leiria and the rest was history.

He went on to assemble one of the most ruthless and tactically astute sides the game has seen, completely blowing everybody’s minds and storming to the Champions League in 2004 by seeing off the likes of Manchester United, Lyon, Deportivo and Monaco along the way.

That was after he’d turned them into league and UEFA Cup winners, too. Iconic.

2. Inter

An extremely harsh second, Mourinho’s spell with the blue side of Milan was perhaps the only time in his managerial career where everything was perfect.

Winning the Scudetto in his first season, the best was yet to come as he built yet another superteam of stars and work horses to guide Inter to the club’s only continental treble to date, in an era where Manchester United and Barcelona felt unstoppable.

He won Serie A again in his final season as well as taking them to another Champions League final, losing to Barcelona in 2010 before heading to Spain himself.

It was an emotional ending for Inter and Mourinho, but one that was right. The only perfect ending in his career to date.

Lovely moment Inter fans serenade their former treble-winning manager José Mourinho 👏

One of the special ones ✨ pic.twitter.com/OG6STi25UF

— Football on TNT Sports (@footballontnt) April 23, 2022

1. Chelsea (2004-07)

“Please don’t call me arrogant, but I’m a European champion and I think I’m a special one.”

That first spell with Chelsea remains unrivalled. Shaking the Premier League to its core with an expensively assembled superteam of defensive goliaths, Mourinho held the title captive in his first two seasons in charge, turning the club into serial winners and setting defensive records that are yet to be matched.

Mourinho’s arrival at Chelsea also saw him present his mind games to the world. Water bottle kicks and touchline scraps, rambling press conferences and an arrogance that couldn’t be contained. It was entertainment we’d never seen before, and it was genius. The perfect way to take pressure off his own team.

It ended sourly in 2007, but neither Mourinho nor Chelsea would change any of it for the world.

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