Carlo Ancelotti, the seasoned Italian manager, has reached a significant milestone in his managerial career: his 300th game in charge of Real Madrid. This monumental achievement is set to take place against Alaves, a fitting opponent in what will be remembered as another chapter in his legendary partnership with the ‘Merengue’ club.

Ancelotti’s journey with Real Madrid is a story told in two parts, each one filled with glory, tactical mastery, and a bond between the manager and the club that transcends the ordinary.

The first chapter of this partnership began in July 2013, when Ancelotti was tasked with leading one of the most demanding clubs in world football. It was a challenging period, but he quickly proved his worth. Under his guidance, Madrid captured their long-awaited “La Decima” — their 10th UEFA Champions League title — in 2014, cementing Ancelotti’s place in the hearts of Madridistas. The Italian’s calm demeanor, coupled with his tactical acumen, earned him admiration both on and off the pitch. His first spell ended in May 2015, but the seeds of a deep connection had been sown.

After years apart, Ancelotti made his return to the Santiago Bernabéu in June 2021, taking the reins of a club that had experienced upheaval and uncertainty. In this second spell, his wisdom and experience revitalized Madrid, leading them to yet another Champions League victory in 2022. His ability to adapt to new challenges while maintaining the core principles of his footballing philosophy made him a revered figure in the dressing room and among fans alike.

Now, as he prepares for his 300th appearance, there is a sense of reflection and anticipation. Ancelotti’s contract runs until June 2026, and although he remains as passionate as ever, he has hinted at retirement when the time comes. By then, he will have written his name in the annals of football history as one of the greatest managers ever to grace the game.

But for now, all eyes are on Alaves and the continuation of a legend in the making.