Thompson, who was signed to a Two-Way Contract by Orlando on February 7, appeared in 31 regular season G League games with the Osceola Magic last season and averaged 18.4 points, 4.9 rebounds, 3.2 assists, 1.03 steals and 34.2 minutes while shooting 40.2 percent from the field, 39 percent from three-point range and 77.3 percent from the foul line. He led the team in three-point field goals made and finished second in points, field goals made and free throws made, helping the team to the number one seed in the Eastern Conference. He recorded 11 20-point games, including two 30-point performances, and connected on multiple three-point field goals 25 times, including a season-high eight from downtown against the College Park Skyhawks on December 27. He also appeared in five playoff games with Osceola on their way to the G League Finals and averaged 21.4 points, 5.6 rebounds, 3.0 assists, 1.00 steals and 36.6 minutes while shooting 47.8 percent from the field, 40.5 percent from three-point range and 86.7 percent from the line.