On October 21, 2019, Hield signed a four-year contract extension. On December 26, Hield accused coaches and teammates of having "trust issues" after he was benched late in regulation of a game that the Kings eventually lost in double overtime to the Minnesota Timberwolves. He apologized to the entire team the next day for his remarks. Hield eventually lost his starting spot to Bogdan Bogdanović, but the switch produced a boost in his production and efficiency; in only his second game off the bench, on January 27, 2020, and again against the Timberwolves, Hield scored a career-high 42 points to lead the Kings to a 133–129 overtime victory. Afterwards, Hield dedicated the game to his idol Kobe Bryant, who died in a helicopter accident the day prior. On February 15, Hield won the Three-Point Contest at NBA All-Star Weekend in Chicago, topping Devin Booker 27–26 in the final round.