Miles appeared in 40 games with the Toronto Raptors in 2018-19 before being traded to Memphis. He appeared in 13 contests with the Grizzlies. He missed the last 12 games of the regular season due to injury. Averaging 16.2 minutes per game over 53 appearances, Miles scored 6.4 points per game, to go with 1.8 rebounds and 0.7 assists and shot 33.0 percent from beyond the arc. Miles recorded at least one steal in 19 games. On Jan. 19, while still a member of the Toronto Raptors, Miles collected five steals in a game against Memphis, the team he'd later be traded to. Miles scored in double figures 15 times, including a season-high 33 points against the Atlanta Hawks on Mar. 13. 65.3 percent of Miles' field-goal attempts last season were threes, finishing 2018-19 with the most three-point shots per 100 possessions on the Grizzlies (11.2). The veteran sharpshooter heated up from distance as the year progressed, converting on 27.1 percent of threes in the first three months of the year (Oct-Dec) before increasing his three-point conversion rate to 39.6 percent between January and March. He has posted six seasons with 100 or more made threes.

Miles played in 70 games for the Toronto Raptors during the 2017-2018 season, but he logged just three starts during that span and averaged 10.0 points per contest. The athletic wing scored a season-high 24 points in a 123-103 win over the Charlotte Hornets on Feb. 11 -- in that game, he made six three-point field goals and shot 72.7 percent from the field. Miles matched that same total of threes made in four other games throughout the season. He pulled down a season-high seven rebounds against the Atlanta Hawks on March 6 as the Raptors won 106-90. Miles played in 10 playoff games for Toronto. He finished with four double-digit scoring games off the bench. In the First Round against the Washington Wizards, he scored 12 in Game 1 and 18 in Game 2. He then scored 13 points in each of the last two games against the Cleveland Cavaliers in the Eastern Conference Semifinals.

The 2016-17 campaign was Miles' 12th season in the NBA and third with the Indiana Pacers. He started 29 of the 76 games he appeared in and averaged 23.4 minutes per game. The long-distance sharpshooter averaged 10.7 points per contest on 43.4 percent shooting. Miles also chipped in 3.0 rebounds and 0.6 steals per game, too. He set a new career best with a 41.3 shooting percentage on three-point attempts. That three-point percentage ranked Miles 12th in the league for the season. In November, Miles had a season-high six-game double-digit scoring streak. During that span, he averaged 17.2 points and 3.5 rebounds on 54.7 percent shooting. He also had a pair of four-game streaks with 10 or more points in December and March. Miles scored a season-high 27 points against the Cleveland Cavaliers on April 2. In four postseason contests, he averaged 7.3 points on 45.8 percent shooting before the Pacers were eliminated by the Cavaliers. Miles started both Game 3 and Game 4 of that series..