In the third game of his sophomore season, on November 16, 2018, Gilyard scored a season-high 31 points, 27 of which came in the second half, and recorded six assists in a 78–70 victory over IUPUI. On February 11, 2019, he was named Atlantic 10 Conference Player of the Week for his first time after averaging 22.5 points, 5.5 assists and five steals per game in wins over George Mason and George Washington. Gilyard averaged 16.2 points, 5.2 assists and 2.8 steals per game as a sophomore, earning second-team All-Atlantic 10 and Atlantic 10 All-Defensive Team honors. He joined Allen Iverson and Jason Kidd as the only Division I players since 1992 to record at least 868 points, 290 assists and 177 steals by the end of their sophomore seasons.
