Jackson appeared in 59 games for the Pelicans during the 2019-20 season. He averaged 6.3 points, 1.4 rebounds, 1.0 assists, 0.3 steals and 0.1 blocks in 13.5 minutes. He shot 40.5 percent from the field, a career-high 32.6 percent from three and a career-high 74.7 percent from the free-throw line. On Jan. 13 against the Pistons, the Duke product established a new career high with eight rebounds across 32 minutes. The 6-foot-3 guard also provided 13 points (5-13 FG, 0-4 3Pt, 3-3 FT), one assist and one steal in that contest. Jackson's other single-game season highs were 31 points (also a career high), six assists, four threes, two steals and one block. Jackson had 15 performances with double-digit points, nine performances with three-plus rebounds and 12 performances with multiple assists. On the defensive end, he had 14 games with at least one steal and four games with at least one block. In the 15 games that Jackson saw 20-plus minutes, he averaged 14.4 points, 2.5 assists, 2.4 rebounds, 0.6 steals and 0.1 blocks. In the six performances that Jackson hit at least three triples, he averaged 20.3 points. After the NBA returned from a hiatus as a result of the coronavirus pandemic, the Pelicans were one of the 22 teams invited to resume play within the Orlando bubble. Appearing in all eight seeding games, Jackson averaged 10.8 points, 2.5 assists, 1.5 rebounds and 0.3 steals across 17.6 minutes. He also had one of the best games of his career in the bubble, posting his career-high 31 points (12-24 FG, 3-9 3Pt, 4-5 FT) along with five assists, two rebounds and one steal across 36 minutes against the Magic on Aug. 13.

After sitting out the previous season recovering following a foot injury, Jackson made his NBA debut on Oct. 17 against the Rockets. He'd reach double-digits scoring in just his third game by dropping 14 points while adding two assists against Utah. He upped his career-high by scoring 17 against Memphis, then surpassed that again in his next game with 19 in only 19 minutes during a win over Cleveland on Jan. 9. Jackson also nailed a season-high four three-pointers in that last matchup. He began to break into the starting rotation in late January, scoring 10 points and seven rebounds in his first attempt against Houston on Jan. 29. Jackson then topped his career-high with a 25-point effort in 42 minutes versus San Antonio on Feb. 2. He would match his seven-rebound total on Mar. 2 against Denver. And on Mar. 24, Jackson would top out at six assists in a contest with Houston on March 24. He started his last nine games of the season, and 16 of his final 26. Jackson finished the campaign averaging 8.1 points and 2.2 rebounds across 61 games before a concussion forced him to miss the final six games of the year.