On 3 August 2011, it was officially confirmed that Cuadrado would join Lecce for the 2011–12 season. He scored his first goal for the club against Cesena, the sole goal in a 1–0 victory. In spite of further impressive performances from Cuadrado, however, Lecce finished 18th and was relegated to Serie B. He would then return to Udinese. Around this time, he was watched by an unidentified English club who deemed that at 23 years he was too old to be signed by the club.