Shaquille O’neal left the Magic as a free agent and moved to Los Angeles Clippers in the offseason of 1996.
They fired coach Brian Hill and replaced Richie Adubato. Despite one of their key players leaving, they still managed to have a winning season with 45-37 record, leading them were Penny Hardaway, Darrell Armstrong and Ron Seikaly. They advanced in the playoffs as they lost to the Miami Heat in 5 games.
In 1997-98 season, they hired Chuck Daly to coach for the team. The season was rampaged with injuries as Nick Anderson and Bo Outlaw were the ones leading the team. They still finished the season with 41-41 record but did not make it to the playoffs. In 1998 draft, they acquired Matt Harpring and Michael Doleac for the 15th and 12th pick respectively.
They also acquired Dominique Wilkins that season. They had a healthy roster and finished the season as the 3rd seed for the playoffs. They faced off against the 76ers in the first round and lost in 4 games.
In 1999, they hired rookie coach Doc Rivers. They traded their superstar Hardaway to the Suns for Danny Manning, Pat Garrity and future drafts. They had a mediocre roster but still managed to have a 41-41 season. Coach Doc Rivers was named the Coach of the Year that season.
They acquired Tracy Mcgrady and Grant Hill from the Free Agency. They were expected to be a dominant force in the league but Hill was limited to 4 games because of a serious ankle injury.
Mcgrady became a star for the Orlando Magic as he become one of the top NBA scorers. With Mike Miller from the draft, they finished the season with 43-39 record, enough to advance in the playoffs. They lost to the Bucks in the first round.
The next season, with Mcgrady leading the team, finished the season with 44-38 as Hill still sidelined with his ankle injury. They moved to the playoffs but lost to Charlotte Hornets in the first round.
In 2002-03 season,they acquired Gordan Giricek and Drew Gooden from the Grizzlies in exchange for Mike Miller. Still, it was Mcgrady leading the team to a 42-40 record.Mcgrady was the top scorer in the league with 32.1 ppg. They still lost in the first round of the playoffs against the Pistons.
The 2003-04 season was tough for the Magic. They struggled despite Tmac leading them with 28 ppg. They finished the season with a disappointing 21-61 record.
The next season, Mcgrady was traded to the Houston Rockets along with Gaines and Tyronn lue and Juwan Howard for Steve Francis, Kelvin Cato and Cuttino Mobley. They also got the number one draft pick Dwight Howard. Howard showcased his talents in his first season and showed hope for the magic as they finished the season with 36-46 record.
The next season, they had a nice run for the playoffs but they were cut short from playoff contention when the Bulls defeated the Heat on April 16.
They advanced to the playoffs the next season as the 8th seed. They were swept by the Pistons in the first round. In 2007, they hired Stan Van Gundy as the head coach and also signed Rashard Lewis. They ended the season with an impressive 52-30 record. They moved to the postseason as the 3rd seed in the Eastern Conference. They defeated the Raptors in five games and moved on against the Pistons the next round. Again, they lost to the Pistons.
Their next season was one of their most successful in years, finishing 59-33 in the season. They advanced in the playoffs facing the 76ers in the first round. They routed the 76ers and moved to 2nd round against the Boston Celtics. They defeated the defending champs and moved on to the conference finals against the Cavaliers. They won over the Cavs lead by LeBron James and moved to the NBA Finals against the Los Angeles Lakers. They lost in 5 games.
In the 2009-2010 season, they finished it with 59-23 record and went to the playoffs. They swept the Bobcats and the Hawks in the first two rounds. They lost to the Boston Celtics in the conference finals.