There are a great many great managers who have never lifted the famous jug-eared trophy, designed to celebrate the best team in Europe.

The formidable Hector Cuper. The revolutionary Valeriy Lobanovskyi. The arch-sophisticate Arsene Wenger. Frankly, the list is long and it’s extremely illustrious.

Their collective non-fulfilment is mentioned here to place into even sharper context the achievements of the ever-calm and all-knowledgeable Carlo Ancelotti, who didn’t lead one side to Champions League glory, nor two like Sir Alex Ferguson, Pep Guardiola and Jose Mourinho. 

On a record four occasions – twice with AC Milan and twice at his present residence Real Madrid - the esteemed coach has managed to sculpt sides that have bested the continent’s elite, each time incidentally winning the competition in style. 

His most recent success was an unexpected one, with Los Blancos not at the absolute peak of their powers and requiring several dramatic comebacks to reach last summer’s final. 

Going into their second Champions League showpiece event with Liverpool in five years, the Spanish giants were the slight underdogs, but a strike by Vinicius Jr on the hour mark overturned the betting odds and settled matters.

For Real it ensured they were European champions for a quite remarkable 14th time. 

And while Madrid wildly celebrated, Ancelotti could take huge personal pride in overtaking Bob Paisley and fellow Los Blancos alumni Zinedine Zidane in becoming the manager with the most Champions League triumphs.

By any and every metric that’s an outstanding feat. Yet it only gets more impressive. 

Last November, in beating Celtic 5-1 at the Bernabeu, the 63-year-old claimed the most Champions League victories, his substantial tally of 103 wins surpassing a record previously held by Sir Alex Ferguson.

There is also the pretty sizable detail that as a player Ancelotti twice attained the ultimate club prize, when he bossed the midfield of AC Milan’s sublime late-eighties creation. 

On six different occasions therefore, the genial genius has attended Champions League victory dinners. Something about the tournament clearly suits him. 

It’s a harmonious relationship that began – from a managerial perspective – in 2003, when a Rossoneri, resplendent with the likes of Nesta, Pirlo and Shevchenko, navigated their way past city rivals Inter in the semis to set up a dream final with Juventus. 

Sadly, the highly anticipated match-up failed to live up to the hype, eking its way to penalties, but for Ancelotti three missed spot-kicks by Juve placed him in rare company indeed. He had now been crowned champion of Europe as a player and manager.

Two years later disaster struck, when Milan capitulated in the second-half to Liverpool in Istanbul but to the club’s enormous credit they recovered well from that mortifying loss, gaining revenge over the Reds in 2007. Filippo Inzaghi was the hero that evening. 

Soon after followed a move to Chelsea, then PSG, before Real Madrid came calling, one of the most prestigious names in world football needing Ancelotti’s Champions League pedigree, having not reached a final for over a decade.

It took the brilliant coach just ten months to give them what they craved. Los Blancos were champions of Europe that May. 

When assessing the Champions League betting for this season, naturally club form comes into it, as too does each contender’s biggest stars.

Do not discount however the importance of the coaches at the helm, or more accurately, the well-dressed man standing thoughtfully in the technical area of the Bernabeu. 

The tournament evidently loves Carlo Ancelotti, and he loves it.

*Credit for all of the photos in this article belongs to AP Photo*


Stephen Tudor is a freelance football writer and fantasy football enthusiast who only knows slightly less about the game than you do.

A contributor to FourFourTwo and Forbes, he is a Manchester City fan who was taken to Maine Road as a child because his grandad predicted they would one day be good.