He saw 67 games in his first full season on the roster in 1996–97, averaging 6 points per game in 15 minutes per game off the bench. Armstrong won the NBA Sixth Man of the Year Award and the NBA Most Improved Player Award in 1999, thus becoming the first player in NBA history to win both awards simultaneously. In a 1999 game against the Philadelphia 76ers, Armstrong stole an inbounds pass and streaked to the other end of the court for a game winning layup as time expired. He subsequently became the starting point guard for the Magic. His career year was in 1999–00, averaging 16.2 ppg in 31 mpg.