The COVID19-shortened 2019-20 season was Kennard's third season in the Association. Kennard appeared in 28 games for the Pistons, with 25 starts. For the season, the 23-year-old set per-game career highs in points (15.8), assists (4.1), rebounds (3.5), threes (2.6) and minutes (32.9). He also shot a career-high 89.3 percent from the free-throw line. On opening night, Oct. 23, Kennard scored a career-high 30 points, with six three-pointers, during a win at Indiana. In a Nov. 6 win over the Knicks, Kennard posted 12 points, a season-high nine rebounds and seven assists. On Nov. 22, the shooting guard dished a career-best nine assists during a big home win over the Hawks. Unfortunately, his season was cut short on Dec. 23 due to a knee injury. Kennard had 10 performances with at least 20 points, three rebounds and three assists. Half of those included at least four made threes. In the eight games that Kennard saw at least 35 minutes of play, he averaged 18.6 points, 4.0 rebounds and 4.0 assists per contest..

In his sophomore season, the 2017 lottery pick averaged 5.7 points on 67 percent shooting in 14 minutes through three games before a shoulder injury sidelined him for over a month. On Dec. 10, the 23-year-old erupted for 28 points on 11-of-18 shooting from the field (including 5-of-8 from downtown) against Philadelphia, opening the door for more minutes as a key cog in Detroit's second unit. Kennard's playing time and performance grew following the All-Star break. After averaging 8.4 points per game on 42 percent shooting from the field pre-break, Kennard's numbers jumped to 11.7 points per game on 47 percent field-goal shooting after the break. On the season, his 39.4 three point shooting percentage ranked 28th in the Association. Kennard foreshadowed his penchant for the spotlight with a 27-point performance against the Knicks in the regular-season finale. That helped Detroit clinch the final playoff spot in the Eastern Conference. He then broke out in the team's first-round matchup against the Bucks. He earned a robust 33 minutes per game and averaged 15.0 points and 4.0 rebounds on 48.9 percent shooting from the field while converting 9-of-15 three-point attempts. The sharpshooter led the Pistons with 21 points in Game 1 and 19 points in Game 2. However, Detroit was ultimately eliminated from the postseason by the Bucks.

Kennard was drafted 12th overall by the Pistons in 2017. The Duke product had a solid rookie season, playing in 73 games and starting nine times. He showed promise early on, tallying 11 points on 5-of-8 shooting in 19 minutes of action in his first NBA contest at Washington. He scored in double digits four times in November and averaged 17.2 minutes during the month. Kennard notched the first 20-point game of his career on Dec. 30 in a home win against the Spurs. He shot 7-of-12 from the field, including 4-of-5 from long range, and grabbed three steals in 30 minutes off the bench. The 21-year-old continued to improve through the month of January, when he scored in double digits six times while averaging 8.1 points and shooting 40 percent from long range. Kennard had a strong finish to the season with an average of 10 points per game while shooting 46 percent from the field in March. He averaged 20.3 points, 5.0 rebounds and 3.6 assists in 33 minutes per game over an impressive three-game streak to close the campaign. This run was capped with a season-high 23 points on 8-of-14 shooting -- including 3-of-6 from long range and 4-of-4 from the free-throw line -- along with five rebounds and five assists at Chicago on April 11.