On December 10, 2019, Adebayo recorded his first career triple-double with a career-high 30 points, 11 rebounds and 11 assists in a 135–121 overtime win against the Atlanta Hawks. On December 14, he had his second career triple-double in a 122–118 overtime win over the Dallas Mavericks, scoring 18 points with 11 rebounds and 10 assists. On December 16, Adebayo was named Eastern Conference Player of the Week for the games played from December 9 to 15, when he averaged 20.0 points, 11.3 rebounds, 8.7 assists per game. On January 27, he recorded 20 points, 10 rebounds and 10 assists in a 113–92 win over the Orlando Magic. On January 30, Adebayo was named to his first NBA All-Star Game. On February 15, he won the NBA All-Star Weekend Skills Challenge competition. At the end of the 2019–20 season, Adebayo finished as runner-up in voting for the Most Improved Player Award. He was also named to the NBA All-Defensive Second Team and finished fifth in voting for the Defensive Player of the Year Award.