Carlo Ancelotti's coaching journey is profoundly intertwined with two iconic clubs: AC Milan and Real Madrid. His relationship with Milan began as a player, where he enjoyed a successful spell in the midfield from 1987 to 1992. 

Ancelotti’s time with the Rossoneri was not only pivotal for his career as a player but also laid the foundation for his future successes as a manager. Between 2001 and 2009, he returned to the club as a coach, leading Milan to remarkable triumphs, including the UEFA Champions League trophy twice, adding to the two titles he had won as a player.

Ancelotti has often expressed that both clubs hold a special place in his heart, with Milan representing his early achievements and Real Madrid symbolizing the pinnacle of his coaching legacy. 

This Tuesday marks a significant milestone for Ancelotti as he prepares to face Milan in the UEFA Champions League for the first time as the manager of Real Madrid. His record against the Rossoneri is impressive, having faced them 15 times, securing five victories and drawing seven, with only three losses.

However, this upcoming clash at the Santiago Bernabéu promises to be uniquely special. It represents more than just another match; it is a reunion with the club where Ancelotti forged much of his identity in football, juxtaposed against the backdrop of his current role at the helm of Madrid. 

As he steps onto the touchline, Ancelotti will experience a whirlwind of emotions, reflecting on a career shaped by the successes and memories created at both clubs. For him, this encounter is not just a professional obligation but a poignant moment that encapsulates his profound connection to both Milan and Madrid.