كأس السوبر الإيطالي
Under the new Milan manager, Vincenzo Montella, De Sciglio started almost every match, mostly as a left-back. On 23 December 2016, he started the match against Juventus in the Supercoppa Italiana, which Milan went on to win 4–3 in a penalty shoot-out, with De Sciglio winning his second Supercoppa Italiana title.