
Carlo Ancelotti returned to Real Madrid after Zidane departed at the end of last season, he had only just signed a long term contract with Premier League club Everton before leaving for Real Madrid calling it a club of his heart. He won the club's 2014 UEFA Champions League La Decima in his first stint.
Ronald Koeman is one of Barcelona's greatest players and one of the highest scoring defenders of his generation. He was a former assistant coach of FC Barcelona in the late 90s and returned to the club at the beginning of the 2020/21 season after Quique Setien was sacked after just eight months in charge.
Carlo Ancelotti is clearly the standout manager among the two having won 19 major trophies at Real Madrid, AC Milan, Chelsea, Bayern Munich and PSG amongst others while Ronald Koeman has only won 10 major trophies at Ajax, PSV and other clubs. Obviously Ancelotti is the richest of the two, he's worth $50m while Koeman is worth $16m.
The two have met four times as managers when Ancelotti was at AC Milan and Koeman was at Ajax. Ancelotti's team won three of the games, the other ended in a draw, which implies that Ronald Koeman is yet to score a victory over Carlo Ancelotti. The two also met once as players representing their countries Netherlands and Italy in a 0-0 friendly match in 1990.

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