On 11 February 2014, Cuadrado scored Fiorentina's second goal of a 2–0 Coppa Italia semi-final second leg victory over his former club Udinese, securing "La Viola" a 3–2 aggregate victory and a spot in the final. He was booked after scoring the winning goal, and suspended for the final, which his team lost 1–3 to Napoli on 3 May.