In June 2018, reports surfaced claiming that Leonard had requested a trade from the Spurs and that he did so after months of tension between his camp and the Spurs stemming from a disagreement over his injury rehabilitation program. A month later, on July 18, Leonard and teammate Danny Green were traded to the Toronto Raptors in exchange for DeMar DeRozan, Jakob Pöltl and a protected 2019 first-round draft pick. It was a risky move for the Raptors and their president, Masai Ujiri, given the concerns over Leonard's health and the possibility of him leaving as a free agent at the end of the season. In his debut for the Raptors in their season opener on October 17, Leonard had 24 points and 12 rebounds in a 116–104 win over the Cleveland Cavaliers. Two days later, he had 31 points and 10 rebounds in a 113–101 win over the Boston Celtics. Leonard was named Eastern Conference Player of the Week for games played November 26 – December 2. On January 1, 2019, he scored a career-high 45 points in a 122–116 win over the Utah Jazz. On January 31, against the Milwaukee Bucks, Leonard's career-high streak of scoring at least 20 points in 22 consecutive games ended when he had 16 points in a 105–92 loss. In Game 1 of the Eastern Conference semifinals against the Philadelphia 76ers, Leonard had a playoff career-high 45 points, on 16-of-23 (69.6%) shooting, to lead the Raptors in a 108–95 victory. He became just the second player in Raptors history to eclipse 40 points in a playoff game, joining Vince Carter (50 points, 2001). In the deciding Game 7, Leonard hit a shot from the corner at the buzzer that bounced off the rim four times before falling to give the Raptors a 92–90 victory over the 76ers to advance to the Eastern Conference Finals. He finished the game with 41 points on 16-of-39 shooting. This was the first Game 7 buzzer beater in NBA history and caused the normally calm Leonard to let out a victorious scream as he was swarmed by his teammates. Leonard said of the shot afterward: "It was great. That's something I've never experienced before, Game 7, game-winning shot. It was a blessing to be able to get to that point and make that shot and feel that moment. It's something I can look back on in my career."