Powell played sparingly for the Raptors over the first half of the 2016–17 season.
With DeMarre Carroll sitting out back-to-back games early on in the season, Powell received a number of starting assignments.
He would rise to the occasion every time he got an opportunity, only to go missing in action for a handful of games before his services were needed again.
On December 20, 2016, Powell scored a season-high 21 off the bench in a 116–104 win over the Brooklyn Nets.
He had three more 21-point games over the next three months.
On April 24, 2017, in Game 5 of the Raptors' first-round playoff series against the Milwaukee Bucks, Powell scored a playoff career-high 25 points to help the Raptors take a 3–2 series lead with a 118–93 win.

On October 8, 2017, Powell signed a four-year, $42 million contract extension with the Raptors.
The deal, which started with the 2018–19 season, included a player option on the fourth year.

On November 5, 2018, against the Utah Jazz, Powell partially dislocated his left shoulder joint, and was ruled out indefinitely.
He returned to action on December 19 against the Indiana Pacers after missing 21 games.
On January 6, 2019, he scored a season-high 23 points in a 121–105 win over the Pacers.
On March 22, he had a career-high 11 rebounds in a 116–109 loss to the Oklahoma City Thunder.
On April 7, he matched his season high with 23 points in a 117–109 overtime win over the Miami Heat.
Powell won his first championship when the Raptors defeated the Golden State Warriors in the 2019 NBA Finals in six games.

In 2019–20, Fred VanVleet became the starting shooting guard after Toronto lost Danny Green in free agency.
Powell began the season scoring in double digits only once in the first seven games.
On November 29, 2019, he scored 19 of his career-high 33 points in the third quarter in a 90–83 win over the Orlando Magic.
As a starter in December in place of an injured VanVleet, he scored 20 or more points in three straight contests for the first time in his career.
Later in the month, Powell injured his shoulder against the Detroit Pistons, and was out for three weeks before returning in mid-January.
On January 31, 2020, he fractured the fourth metacarpal of his left hand against the Pistons.
He returned at the end of February after missing nine games.
On March 5, Powell scored a career-high 37 points in a 121–113 win over the Golden State Warriors.
After averaging a conference-leading 31.3 points on 56 percent shooting and helping the Raptors win three road games that week, he was named the NBA's Eastern Conference player of the week for the first time in his career.
Powell played sparingly for the Raptors over the first half of the 2016–17 season. With DeMarre Carroll sitting out back-to-back games early on in the season, Powell received a number of starting assignments. He would rise to the occasion every time he got an opportunity, only to go missing in action for a handful of games before his services were needed again. On December 20, 2016, Powell scored a season-high 21 off the bench in a 116–104 win over the Brooklyn Nets. He had three more 21-point games over the next three months. On April 24, 2017, in Game 5 of the Raptors' first-round playoff series against the Milwaukee Bucks, Powell scored a playoff career-high 25 points to help the Raptors take a 3–2 series lead with a 118–93 win.
On October 8, 2017, Powell signed a four-year, $42 million contract extension with the Raptors. The deal, which started with the 2018–19 season, included a player option on the fourth year.
On November 5, 2018, against the Utah Jazz, Powell partially dislocated his left shoulder joint, and was ruled out indefinitely. He returned to action on December 19 against the Indiana Pacers after missing 21 games. On January 6, 2019, he scored a season-high 23 points in a 121–105 win over the Pacers. On March 22, he had a career-high 11 rebounds in a 116–109 loss to the Oklahoma City Thunder. On April 7, he matched his season high with 23 points in a 117–109 overtime win over the Miami Heat. Powell won his first championship when the Raptors defeated the Golden State Warriors in the 2019 NBA Finals in six games.
In 2019–20, Fred VanVleet became the starting shooting guard after Toronto lost Danny Green in free agency. Powell began the season scoring in double digits only once in the first seven games. On November 29, 2019, he scored 19 of his career-high 33 points in the third quarter in a 90–83 win over the Orlando Magic. As a starter in December in place of an injured VanVleet, he scored 20 or more points in three straight contests for the first time in his career. Later in the month, Powell injured his shoulder against the Detroit Pistons, and was out for three weeks before returning in mid-January. On January 31, 2020, he fractured the fourth metacarpal of his left hand against the Pistons. He returned at the end of February after missing nine games. On March 5, Powell scored a career-high 37 points in a 121–113 win over the Golden State Warriors. After averaging a conference-leading 31.3 points on 56 percent shooting and helping the Raptors win three road games that week, he was named the NBA's Eastern Conference player of the week for the first time in his career.
Norman Powell