Since the UEFA Champions League was rebranded in 1992, winning it has remained the pinnacle of club football success, and only a few managers have done it more than once. At the very top stands Carlo Ancelotti, the undisputed king of the Champions League sidelines, with five titles to his name. He is not just the most decorated manager in the modern era of the competition; he has also achieved legendary status by mastering the tournament across generations, clubs, and tactical eras.
Following him are Pep Guardiola and Zinedine Zidane, both tied at three wins each. Guardiola's wins span from his tiki-taka revolution at Barcelona to his more refined dominance at Manchester City. Zidane, on the other hand, achieved a historic feat by winning it three times in a row with Real Madrid—a run that remains unmatched in the Champions League era.