Armstrong first signed with the NBA as a free agent for the Orlando Magic in late 1994–95, playing in the last 3 games of the regular season with 10 points in 8 minutes of action including a spectacular one-handed reverse windmill dunk late in a blowout vs the Indiana Pacers in his 2nd game. In 95–96 he played just 41 minutes in 13 games, scoring 42 points total; despite his limited minutes, he participated in the 1996 Slam Dunk Contest. He was inactive after February.