Milton's third season with the 76ers was his best yet as he set a few career-highs while playing a more important role in his team's rotation. The former SMU guard notched career-best season averages of 13.0 points, 3.1 assists, 2.3 rebounds and 0.6 steals. Milton posted an average of 23.2 minutes of action while playing in 63 games and starting in four. The guard hit 45.0 percent from the field, 35.0 percent from beyond the three-point arc and 83.0 percent from the free-throw line. One of Milton's best games of the season came against the Magic on May 16, where Milton dropped a career-best nine assists to go along with 15 points, four rebounds, two blocks and a steal. Milton became a consistent scoring threat in his third year as he recorded 45 double-digit scoring performances on the year after only recording 21 in the 2019-20 season. One of his best scoring performances on the year came against the Heat on Jan. 14, where the guard dropped a season-high 31 points, to go with seven assists, two rebounds, two steals and a block. Defensively, Milton established himself as a solid defender who recorded 33 games with at least one steal and 15 games with at least one block. His best defensive performance came on Dec. 23 against the Wizards, as Milton snagged three steals in 30 minutes. In the playoffs, Milton recorded an average of 4.3 points, 0.8 rebounds and 0.8 assists in 10.0 minutes.2019
In his second NBA season, Milton appeared in 40 games for the 76ers, making 24 starts and averaging 20.1 minutes per game. The 2018 second-round pick posted career-highs in points (9.4 PPG), rebounds (2.2 RPG) and assists (2.6 APG) per game, while also notching career-bests in field goal (48.4%), three-point (43.0%) and free throw (78.5%) percentage. Milton became a regular in the rotation in January and made his first start of the season on Jan. 25 against the Lakers. In that game, Milton finished with seven points, nine rebounds, and three assists. In a Jan. 30 matchup against Atlanta, Milton posted 27 points, including five three-pointers, to go with five rebounds and six assists. He went for a career-high 39 points against the Clippers on Mar. 1, going 7-of-9 from beyond the arc. Over his final seven games before the suspension of the season, Milton averaged 19.4 points, 4.1 assists, 2.4 rebounds, 1.3 steals and 0.6 blocks, while shooting 60.5 percent from three. Milton started all four of the Sixers' postseason games in Round 1 against Boston. He made his playoff debut in Game 1 of the series, going for 13 points and three assists. Milton established a playoff-career-best with 17 points in Game 3.2018
Milton came off the bench to play 20 games with the 76ers during the 2018-19 season. He averaged 4.4 points and 1.8 rebounds per contest in limited playing time. Milton came off the bench to make his season debut against the Washington Wizards on Nov. 30. In that game, he scored five points and contributed a pair of assists. Milton scored a career-high 13 points against the Orlando Magic on Mar. 25. His career high in rebounds came Apr. 9 against the Miami Heat when he pulled down eight boards. As a two-way player, Milton also competed regularly for the Delaware Blue Coats of the G League. For the Blue Coats, he started 27 games, averaging 24.9 points and 5.3 assists. That scoring rate was good for fourth in the league.