The 1998–99 NBA season was the tenth season for the Orlando Magic in the National Basketball Association. During the offseason, the Magic signed free agents Isaac Austin and All-Star forward Dominique Wilkins. After dealing with injuries the previous season, Anfernee Hardaway played a full season, but would no longer be the same leading the team with just 15.8 points per game. The Magic played solid basketball winning 14 of their first 18 games, and finished the lockout-shortened season second in the Atlantic Division with a 33–17 record, returning to the playoffs as the #3 seed in the Eastern Conference after a one-year absence. Guard Darrell Armstrong had a breakout season winning both the Sixth Man and Most Improved Player awards. However, in the first round of the playoffs, the Magic lost to the 6th–seeded Philadelphia 76ers in four games.

Following the season, head coach Chuck Daly retired, Hardaway was traded to the Phoenix Suns,Nick Anderson was traded to the Sacramento Kings after ten seasons with the Magic, Horace Grant was dealt to the Seattle SuperSonics, Austin was sent to the Washington Wizards, and Wilkins along with his brother Gerald Wilkins both retired.

For the season, the Magic changed their uniforms which lasted until 2003.

(3) Orlando Magic vs. (6) Philadelphia 76ers: 76ers win series 3-1

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