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.
June 21, 2018Drafted by the Dallas Mavericks in the 2nd round (54th pick) of the 2018 NBA Draft and traded to the Philadelphia 76ers for Kostas Antetokounmpo and Ray Spalding.
July 26, 2018Signed a two-way rookie contract with the Philadelphia 76ers.
July 7, 2019Converted from a two-way contract to a regular contract by the Philadelphia 76ers.