Before Ancelotti was a Champions League-winning manager, he won the competition – then called the European Cup – in back-to-back years as a player.

The then-29-year-old midfielder started alongside Paolo Maldini, Franco Baresi and Marco van Basten – among plenty of other legendary names – in both the 1989 and 1990 European Cup finals for, arguably, the finest AC Milan side of all time.

The Rossoneri beat Steaua Bucharest 4-0 and Benfica 1-0 in respective finals, though his most memorable contribution came in the 1989 semi-final second leg at home to Real Madrid.

Ancelotti’s spanked long-range finish, after expertly jinking past two players, to open the scoring in a 5-0 victory ensured his place in AC Milan folklore.

But his achievements after returning as manager in 2001 elevated him even further.

Ancelotti won the Champions League twice during his eight years as manager. In 2003, they ended a nine-year wait for the trophy by beating Juventus, while in 2007, AC Milan avenged their penalty defeat to Liverpool in Istanbul two years before.

He is one of just seven people to have won the tournament as both a player and manager, including Zinedine Zidane, Pep Guardiola and Johan Cruyff. But more on them later.


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Simeone, El Cholo or a 24-carat shithouse.

Whatever you call him, the abrasive Argentine has become an icon at Atletico Madrid thanks to his uncompromising style, touchline enthusiasm and a few trophies along the way.

Despite playing for seven different clubs across a 19-year career, Simeone was at home with Atleti – for whom he had two spells as a player, from 1994-97 and 2003-05.

On leaving for the second time, he said: “I couldn’t stop crying. I didn’t want to go. But… I wanted to be back as manager.”

In 2011, he achieved that. Within five years, they had won La Liga, the Copa del Rey and twice been a Champions League runner-up.

Simeone wrote: “If I want something, I go after it ad nauseam” in a Guardian article in September 2019.

Given his side’s stubbornness – they have had La Liga’s best defence for six of the last eight seasons – and undying work ethic, it’s fair to say the team are one in his image.


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The greatest compliment you can give Zinedine Zidane the manager is that the Europe-conquering version of Real Madrid is difficult to envisage without him at the helm.

Zidane the player, meanwhile, is woven into early 21st-century success of Real Madrid’s Galacticos.

While that period was fallow in comparison, winning only the 2001/02 Champions League and 2002/03 La Liga title during his five years at the club as a player, his ability to stand out among the biggest names in world football at the time cannot be underestimated.

His volley against Leverkusen, from an impossible height and with his weaker foot, to win the Champions League is worthy of legendary status alone.

Yet as a manager, his achievements eclipse even that.

Between 2016 and 2018, Zizou guided the club to an unprecedented hat trick of Champions League titles.

He is one of only three managers to have lifted the trophy three times and remains the only one to do so three years in a row.


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Simply put, it is impossible to consider Barcelona in the last 30 years without picturing Pep Guardiola in some form.

As a player, he was the defensive pivot of Johan Cruyff’s Barcelona Dream Team, which won the 1992 European Cup and four straight La Liga titles between 1990 and 1994.

He was considered by the Dutchman as “one of the best midfielders of a generation”.

Guardiola also captained the side to another two league titles in in 1998 and 1999.

In the dugout, he hasn’t done badly either.

Like someone with cheat codes for Football Manager, the Spaniard has achieved blanket success at Barcelona, Bayern Munich and Manchester City.

That is at least in part down to the strong relationships formed with his players – at the Etihad, he can often be seen coddling Raheem Sterling as he walks off the pitch.

Such was the dressing-room bond he had at Barcelona, Dani Alves once said of him: “If Pep once told me to throw myself off the second tier of the Camp Nou, I’d think: ‘There must be something good down there.’”

From winning a continental treble during his first season in charge of Barcelona in 2008/09 – becoming only the fifth European side ever to do so – to breaking almost every record imaginable with City, he is an unstoppable force.


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Brilliance is often hard to quantify, but when footballing royalty like Sir Alex Ferguson, Arsene Wenger, Pep Guardiola and Xavi – among plenty of others – have all cited Cruyff has an influence in their careers, there is little debate to be had.

On the pitch, he won three European Cups with the formidable Ajax side of the 1970s, carried his country to the World Cup final for the first time in 1974 and fathered the Cruyff Turn.

The Dutchman was the on-field conductor of Ajax’s revolutionary total football tactic. As Eric Cantona said during an interview in 2016: “Ajax changed football and he was the leader of it all.”

On the touchline, Cruyff built dynasties at both Ajax (1985-88) and Barcelona (1988-96).

His coaching philosophies are widely regarded to have helped lay the foundations for Ajax’s European success in the ‘90s – they won the 1991/92 UEFA Cup and 1994/95 Champions League.

His legacy in Spain is visible in the success of modern Spanish football at club and international level and possession-based style, which he fostered at Barcelona.

Cruyff, according to Xavi, “created Barcelona’s DNA”.

Pep Guardiola, meanwhile, once said of him: “Johan Cruyff painted the chapel, and Barcelona coaches since merely restore or improve it.”

It doesn’t get better than that.

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