On 30 August 2019, Smalling joined Serie A club Roma on loan for the 2019–20 season, with the club paying €3 million to sign him. On 24 November 2019, he became the first English player to score at least two goals in the same Serie A campaign since David Beckham during the 2008–09 season, and third overall since 2000 after Jay Bothroyd in the 2003–04 season.