Oladipo would be selected as an All-Star reserve again for the 2019 game. However, while playing against the Toronto Raptors on January 23, 2019, he left the game with a ruptured quad tendon, and he was ruled out for the rest of the season. Regardless, the Pacers again finished the season going 48–34 and secured a playoff spot for the fourth consecutive time on March 22, but were swept in the first round of the 2019 playoffs by the Boston Celtics.