In 2019–20, Love clashed with new Cleveland head coach John Beilein, who was replaced mid-season by J. B. Bickerstaff. Love had five 30-point games during the season, finishing with averages of 17.6 points on 45% shooting and 37.4% from 3-point range while adding 9.8 rebounds and 3.2 assists. In the first preseason game of 2020–21, he sufferered a calf injury which caused him to miss the regular season opener. Love returned in the second game, but he reagravated the injury in the third game and was expected to be sidelined 3–4 weeks.