In the aftermath of LeBron James' departure in free agency to the Los Angeles Lakers, the Cavaliers aggressively pushed to secure Love for the long term. On July 24, 2018, Love signed a four-year, $120 million extension with the Cavaliers. He appeared in the first four games of the regular season before being sidelined with an injured left foot. On November 2, Love had surgery to rectify a painful big toe injury on his left foot. The injury had bothered him since the preseason opener and affected his ability to walk. He was initially ruled out for six weeks, but that was later pushed back to the new year. Love returned to action on February 8, 2019, after missing 50 games. He started and played the first six minutes against the Washington Wizards, scoring four points, before not returning to the game. On February 23, he scored a season-high 32 points in a 112–107 win over the Memphis Grizzlies. For the season, Love attempted 6.7 three-point shots per game, accounting for 52% of his field-goal attempts.