イタリアダービー
Cuadrado returned to Chelsea on 30 June 2016 and played a few friendlies for Chelsea, including the 2016 International Champions Cup. On 31 August, however, Cuadrado returned to Juventus on a three-year loan for €5 million per season, plus a conditional obligation to buy the full registration rights of Cuadrado from Chelsea for an additional €20 million (or €15 million and €10 million in the second and the third year of loan respectively), after certain sports related achievements. Chelsea would also receive a maximum of €4 million bonuses, making the fee potentially raise to €29 million. He was assigned the number 7 shirt at this time. Cuadrado scored his first league goal in nine months on 5 February 2017, scoring the only goal in a 1–0 home win in a "Derby d'Italia" clash with Inter Milan.