There are very few modern-day managers who you’d argue have success ingrained into their genetic makeup. Even the most partisan of Pep Guardiola followers, for example, will be happy to admit the Spaniard hasn’t exactly been at his best at Manchester City this season.

Similarly, José Mourinho, despite success during his stints at Porto, Inter and Chelsea (certainly the first time around), has had a rocky few years trying to replicate his early achievements at the likes of Real Madrid, Chelsea (for the second time) and, of course, Manchester United. Look further afield and you’ll find similarly high-profile managers with blots on their records, see: Louis van Gaal’s reign as Manchester United manager or Jürgen Klopp’s final season at Dortmund.

With Bayern Munich manager Carlo Ancelotti, things are rather different, however. His Reds side, who are 1/40 to win Germany’s Bundesliga, also stand a very good chance of winning one competition that has eluded Bayern in recent times, the Champions League. Should Ancelotti be able to do what his rival Guardiola never could this season, would this success prove to be staunch evidence of what we suspected all along, that Ancelotti is a natural-born winner?

Now a veteran of European football, Italian-born Ancelotti made his name as a titan of football management during his nine-year stint as manager of AC Milan, overseeing a side whose line-up can still make one vehemently foam at the mouth. With Kaká on one flank and Seedorf and Pirlo pulling the strings in the middle, it was a star-studded side that Ancelotti consistently got the best out of. It’d certainly be fair to say that not since Sir Alex Ferguson has club football had a manager like Ancelotti, at least in terms of how unfazed he is by managing some of the world’s most volatile players.

With the Champions League quarter-final draw made, Bayern face their toughest test yet as they take on Ancelotti’s old club Real over two legs. On 12 April and 18 April, much of the world, not to mention the vast swathes of bars that line the Bavarian streets of Munich, will all watch in anticipation as two technically flawless sides do battle under the night sky.

Can the Italian dismantle a Los Blancos side who have proven so dominant in European football as of late? One gets the feeling that this could be the litmus test that defines Ancelotti’s career. 

The 57-year-old will no doubt relish the prospect of defeating a Real side who rather harshly discarded him like yesterday’s news just a few seasons ago. And whilst he’s been no stranger to bringing home the big-eared trophy throughout his career, under the circumstances this year’s cup could turn out to be the sweetest of them all.

With more big names than you can shake a stick at – on the touchline as well as on the pitch – whatever the outcome, Bayern’s quarter-final tie with Real will surely be one to savour.