In 1989 Skiles was selected by the newly formed Orlando Magic in the NBA expansion draft. Mainly a backup point guard, he scored 7.7 points and posted 4.8 assists in 20.9 minutes per game in 70 games, 48 off the bench. In 1990–91 he transitioned to a starting role at the position, jumping to a career high 17.2 points and improved 8.4 assists in 34.4 minutes over 79 games and 66 starts. The season was highlighted on December 30, 1990, when Skiles racked up 30 assists in Orlando's 155–116 victory over the Denver Nuggets at Orlando Arena, breaking Kevin Porter's NBA single-game assists record (29). His well more than doubling scoring and nearly doubling his assists marks from the previous year earned him the NBA Most Improved Player Award.