At the start of the 2013–14 season, Emanuelson returned to the first team and made his first appearance of the season, playing in the left–back position, in a 1–1 draw against PSV Eindhoven in the first leg of the UEFA Champions League Play–Off Round. Since returning from a loan spell from the previous season, Emanuelson continued to establish himself in the left–back position, though he faced competition from Kévin Constant. At times, Emanuelson appeared three times in a midfield positions for AC Milan. He then contributed three assists for the club, winning all three matches. As the 2013–14 season progressed, competitions increased further between the two that saw both of them alternating the starting line–up and substitute role. Despite suffering injuries on two occasions throughout the 2013–14 season, Emanuelson made thirty–three appearances in all competitions. Following this, he was released by the club upon expiry of his contract.