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 five occasions – twice with AC Milan and three times 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. 

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His most recent success was not an unexpected one, with Los Blancos at the absolute peak of their powers and completing a famous La Liga / Champions League double. 

Going into the Champions League showpiece with Borussia Dortmund at Wembley, the Spanish giants were favoured in the betting odds but Los Blancos needed two late goals to clinch the win.

For Real it ensured they were European champions for a quite remarkable 15th time. 

And while Madrid wildly celebrated, Ancelotti could take huge personal pride in cementing his status as the manager with the most Champions League triumphs - he truly is in a league of his own when it comes to Europe's elite club competition.

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

In November 2022, in beating Celtic 5-1 at the Bernabeu, the 63-year-old claimed the record for the most Champions League victories, his substantial tally of 103 wins surpassing the tally 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 Seven different occasions therefore, the genial genius has attended Champions League victory dinners. Something about the tournament clearly suits him and he will go down as an all-time great in the competition. 

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.

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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 coming 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 the photos in this article belongs to Alamy*

Stephen Tudor is a freelance football writer and sports enthusiast who only knows slightly less about the beautiful 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.