Dembélé suffered from a recurring injury to his foot that caused him to miss a number of games in the 2016–17 season. Tottenham's manager Mauricio Pochettino nevertheless described Dembélé as a "genius" in April 2017, and among the best he had worked with, including Diego Maradona and Ronaldinho. Pochettino related that he had said to him: "If we had taken you at 18 or 19 years old, you would have become one of the best players in the world." He underwent surgery on his ankle in May 2017 but thought that he would never be 100% fit again. In the 2017–18 season, he again injured his ankle in the EFL Cup tie against Barnsley in September. However, he gained plaudits for his performances later in the season as a midfielder.