Leonard debuted for the Clippers on October 22, 2019, where he put up 30 points, 6 rebounds, and 5 assists in a 112–102 win over the Los Angeles Lakers. On October 24, he recorded 21 points and tied a career-high 9 assists in a 141–122 win over the Golden State Warriors. On December 11, Leonard returned to Toronto for the first since joining the Clippers and was met with a tribute and a standing ovation from the crowd before scoring 23 points and recording six assists in 112–92 win over the Raptors. Two days later, Leonard scored a then season-high 42 points along with 11 rebounds in a 124–117 win over the Minnesota Timberwolves. It was the first time in franchise history that two players eclipsed 40 points, as teammate Paul George scored 46 points. On Christmas Day, the Clippers and Lakers met once again in a much anticipated matchup, in which Leonard put up 35 points on 11-of-19 shooting and 12 rebounds to lead the Clippers to a 111–106 comeback win despite trailing by as much as 15. On January 14, 2020, Leonard scored a season-high 43 points in just 29 minutes in a 128–103 win over the Cleveland Cavaliers. He was named Western Conference Player of the Week for games played from January 13 through 19. On January 24, Leonard recorded his first career triple-double with 33 points, 10 rebounds, and 10 assists in a 122–117 win over the Miami Heat. On February 16, Leonard was named the NBA All-Star Game MVP of the 2020 NBA All-Star Game.