1989/90: Four years after local developer and banker Jim Hewitt began promoting the idea of an NBA franchise in Orlando. To get things moving e lured then Philadelphia 76ers General Manager Pat Williams to Florida, and together they went to work selling merchandise, while persuading locals to make $100 deposits on season-ticket reservations, to convince the NBA to give them an expansion team. The dream finally became a reality on November 4th as a sold out crowd watched the Magic lose their first ever game at the Orlando Arena 111-106 to the New Jersey Nets. Two nights later Magic fans would get to enjoy their team's first win as the Magic stunned the New York Knicks 118-110. However, there would not be much success that first year as the Magic finished last in the Central Division with a typical expansion like 18-64 record 

1995/96: Despite losing Shaquille O'Neal for the first 22 games the Magic weathered the storm early as Anfernee Hardaway picked up the slack during Shaq's absence leading the Magic to a solid 17-5 start. Shaq would return and would be dominate again leading the way with 26.6 ppg as the Magic won their 2nd straight division title with a record of 60-22. In the playoffs the Magic dominated sweeping the Detroit Pistons in 3 straight before dispatching the Atlanta Hawks in 5 games to set up a much-anticipated showdown with the Chicago Bulls in the Eastern Conference Finals. However, the anticipated match up turned into a mismatch as Michael Jordan motivated by losing to the Magic a year earlier dominated, leading the Bulls to an easy 4-game sweep. Following the season the Magic would be stunned by Shaquille O'Neal who decided to sign a free agent deal with the Los Angeles Lakers, in order to future an acting career which he worked on throughout the off season staring in such Airplane classics as "Kazaam and Blue Chips."
2005/06: The Magic got started off on the wrong foot as they were unable to sign first round draft pick Fran Vazquez, who chose to stay in Europe. Meanwhile Grant Hill was bitten by the injury buy again as a hernia limited him to just 21 games and a 15.1 ppg, as the Magic started 0-3, and sank early in the Southeast Division standings. Steve Francis would be the team's leading scorer, but management had grown tired of his selfish play on the court, as they felt it was hurting the development of Jameer Nelson and Dwight Howard. As the trade deadline approached the Magic decided to head in a different direction, first they acquired Darko Milicic and Carlos Arroyo from the Detroit Pistons in exchange for Kelvin Cato and a 2007 draft pick, and then they dealt Francis to the New York Knicks for Trevor Ariza and Anferne Hardway. However, there would be no Orlando homecoming for Penny, as he was immediately released following the trade. Not surprisingly the Magic struggled after the deals dropping to 20-40 on March 6th, but as the new team started to gel the Magic suddenly got hot and made a late push for the playoffs by winning 16 of their next 20 games. However, in the end the hole was too deep as they fell 4 games short of the 8th seed while posting a record of 36-46.