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Can Ancelotti, Guardiola, Mourinho, Di Matteo win Champions League again?

The Champions League round of 16 kicks off Tuesday and, ahead of the return of European club football's elite competition, ESPN FC is asking -- and answering -- a series of "burning questions."

The third in the series sees Gab Marcotti assess the managers left in the competition who have past experience of winning the European Cup.

There are 16 managers left in the Champions League. Four of them -- Pep Guardiola, Carlo Ancelotti, Jose Mourinho and Roberto Di Matteo  -- have won it before. The other 12 have not.

And that has its own unique resonance in terms of how we view managers because, if any one of that quartet win it again, the needle will move. Records will be set, legacies re-evaluated.

Should Real Madrid win it, Ancelotti would move up to four European Cups, setting a new mark and leaving behind Liverpool's Bob Paisley at three. Even reaching the final would see the Italian do so for the fifth time, which would give him lone possession of that record (he currently shares it with Sir Alex Ferguson and Miguel Munoz).

By winning, Ancelotti would also become the first person to retain the European Cup in the Champions League era. Indeed, the last time a team repeated as European champion was Ac Milan in 1990, who were managed by Arrigo Sacchi and featured Ancelotti as a player.

A win for Bayern Munich would move Guardiola alongside Paisley and Ancelotti. He'd also become the sixth manager to win European Cups with two different teams (after Ancelotti, Jupp Heynckes, Ottmar Hitzfeld, Ernst Happel and Mourinho).

Given that he'll be 44 years old in May -- eight years younger than Mourinho, 12 younger than Ancelotti -- Guardiola would cement his status as one of the most precocious managers ever. In fact, at the rate he's going, should he choose to bounce between juggernaut clubs for the next 20 years, he might even reach double figures. (Though, from what we know of Pep, it's extremely unlikely that he would do such a thing.)

Mourinho too would move to the top rung of European Cup-winning managers if Chelsea go all the way. The twist with him is that he would win it with three different clubs -- Porto, Inter and Chelsea -- and that's something nobody has ever achieved.

And Di Matteo? It's easy to forget that the Schalke boss also has a European Cup under his belt even though he won it less than three years ago. Obviously, Schalke aren't amongst the favorites, but then neither were Chelsea in 2011-12. If the German side somehow managed to win it all, he'd be the first to do it twice as a midseason replacement.

In some ways, it's fitting that these four should make history, because each, in his own way, epitomizes a different archetype of modern managers. What they all share is that they're an expression of the modern, globalized game.

Carlo Ancelotti lead Real Madrid to glory in 2014, having previously won with AC Milan in 2003 and 2007.

Ancelotti spent his playing career and early managerial years in Italy, but since 2009 he has worked abroad in England, France and now Spain, at every stop taking charge of a sharply multinational team.

Guardiola is a dyed-in-the-wool Catalan who rounded out his playing days with stints in Italy, Qatar and Mexico. He got his coaching debut at Barcelona and won plenty of silverware there, but during his year's sabbatical prior to taking the Bayern job, he opted to live in New York City.

Mourinho? He spent four years as an assistant at Barcelona, moved back to Portugal, and then had spells in the Premier League, Serie A and La Liga before returning to Chelsea.

As for Di Matteo, we're talking about a guy born and raised in Switzerland, who played in Italy and England and managed in three different tiers of the English pyramid. Now he's in Germany, which is a natural fit, given that German is his first language and one of four he speaks fluently.

Thus, while there's plenty that obviously divides these four men, from style to footballing philosophy, there's also an obvious worldview, a globalized, cosmopolitan outlook. Di Matteo and Guardiola played at the highest level in the post-Bosman era, so for them, the idea of different nationalities and cultures blending on a football pitch is something they lived through.

Ancelotti and Mourinho experienced it as coaches, but it's no less strong. You get the sense that they don't see nationalities or cultural baggage, they just see players.

There's a fundamental flexibility and pragmatism to all four in terms of how they relate to players, fans and their employers. Guardiola may be the most dogmatic -- the other three have earned the reputation as "players' coaches" -- but even that is tempered by the variety of formations and tactical schemes he experiments with.

Jose Mourinho has reached the Champions League semifinals three times in the past with Chelsea.

Beyond that, differences emerge. Ancelotti is folksy, the ultimate diplomat who avoids conflict and controversy whenever he can, while Mourinho embraces battle, loves to instill a siege mentality, and is not shy when it comes to sniping at everyone from referees to opponents.

Guardiola channels the tortured genius, the utopian whose philosophy drenches everything he does and who is his own worst critic. Di Matteo, on the other hand, is more detached and cool, more pragmatic and perhaps rooted in the real world than the other three. (He also hasn't had the wealth of resources the others have enjoyed and, in that sense, he's more representative of the vast majority of managers.)

If you're a betting man or woman, there's a strong chance this year's Champions League-winning manager won't be lifting the trophy for the first time.

If so, though, he'll still be making history and cementing his spot in football lore and, if it happens, at least some of it will have to do with the global education he received in previous years.

Gabriele Marcotti is a senior writer for ESPN FC. Follow him on Twitter @Marcotti.

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