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Cuadrado won four Coppa Italia titles with Juventus. He was a key member of the team during their dominant period in the competition, helping them secure the trophy in the 2014-15, 2015-16, 2016-17, and 2017-18 seasons. Cuadrado's contributions on the wing, both offensively and defensively, played a significant role in Juventus's success in the Coppa Italia.