In the second round of the Winston-Salem tournament, Cerúndolo defeated Dhakshineswar Suresh, while Báez eliminated Hugo Grenier. Peruvian Ignacio Buse also advanced by beating Adam Walton. On the other hand, Mariano Navone and Daniel Vallejo were eliminated. The surprise of the day came from Martin Damm Jr., who triumphed over world number one, Daniil Medvédev. Other unexpected results also marked this phase.