Five days after signing, Cuadrado made his Chelsea debut after replacing Willian for the last ten minutes of a 2–1 win away against Aston Villa. On 11 February, he made his first start in his first appearance at Stamford Bridge, playing the first 70 minutes before being replaced by Cesc Fàbregas in a 1–0 win against Everton. He won his first Chelsea trophy on 1 March as the club defeated rival club Tottenham Hotspur 2–0 in the League Cup final, coming on in the 76th minute for Willian.