Garland was selected with the fifth overall pick in the 2019 NBA Draft by the Cavaliers. The Vanderbilt product made his NBA debut during the first game of the season, Oct. 23 against the Magic. Garland started, played 32 minutes and recorded eight points (3-9 FG, 2-4 3Pt), five assists, two rebounds and one steal. In his 59 appearances, the rookie averaged 12.3 points, 3.9 assists and 1.9 rebounds in 30.9 minutes per game. He shot 40.1 percent from the field, hit 1.8 threes per contest while shooting 35.5 percent from behind the arc, and shot an impressive 87.5 percent from the free-throw line. On Nov. 22, the young guard scored a career-high 23 points, plus added four dimes, during a loss at Dallas. His longest streak of double-digit scoring was 15 games from Dec. 28 through Jan. 25. Across that stretch, Garland averaged 14.9 points on 13.7 shots, 4.9 assists, 1.7 rebounds and 1.0 steals in 34.4 minutes. On Jan. 14, Garland double-doubled in a road game versus the Clippers. In that game, he posted 14 points, a career-high 10 assists and one steal. During the pandemic-shortened season, Garland had 14 games win which he hit three or more three-pointers. Twice Garland hit five three pointers in a game.