On January 29, 2020, he made his return to the NBA, 371 days after being injured. Coming off the bench for the Pacers, he scored 9 points in 21 minutes of playing time, including a game-tying three-pointer, in an overtime win over the Chicago Bulls. After the game, an emotional Oladipo dedicated the shot to Kobe Bryant and eight other lives lost in a California helicopter crash, three days prior.