February 2: Jameer Nelson left a game after dislocating his right shoulder. One day later, it was announced that he suffered a torn labrum, and would require surgery to repair it, meaning he would likely miss the rest of the season. A few days prior to the injury, Nelson had been named as a reserve in the All-Star Game.
February 25: The Magic were assured a winning season after defeating the New York Knicks.
March 11: The Magic clinched a playoff spot with a win over the Chicago Bulls.
March 25: After beating the Boston Celtics, the Magic clinched their second consecutive division championship. With the win, they were also guaranteed of finishing the regular season with more wins than the previous season.
April 15: The regular season ended, with the Magic finishing one win shy of matching a franchise record.
April 28: Rookie Courtney Lee was accidentally hit in the face by Dwight Howard during Game 5 of the Magic's first round playoff series. The following day it was announced he would miss Game 6, suffering a fractured sinus.
April 29: Dwight Howard was suspended for one game by the NBA for an incident in which Howard elbowed a Philadelphia 76ers player in the face the previous night in Game 5 of the Magic's first round playoff series.
April 30: The Magic advanced to the second round of the NBA playoffs after defeating the Philadelphia 76ers in 6 games.
May 17: In a Game 7 on the road, the Magic advanced to their first Eastern Conference Finals appearance since 1996 after defeating the defending world champion Boston Celtics.
June 9: The Magic earned their first NBA Finals game victory in franchise history. They beat the Los Angeles Lakers in Game 3 at Amway Arena by a score of 108-104. The Magic shot an NBA Finals single-game record 75% in the first half, and a record 62.5% for the entire game. The Magic had lost their first six NBA Finals games (four in 1995 and two in 2009).
June 14: The Magic's season ended, having lost the NBA Finals in five games to the Lakers.
The first half of the 2008–09 season went very well for the Magic. After 41 games, the Magic were 33–8, leading the Southeast Division, as well as having one of the top four records in the league. On January 13, 2009, they scored an NBA record 23 three-pointers against the Sacramento Kings. Nine of the twelve Magic players who played that night scored at least one three pointer. At the start of February, Jameer Nelson, their all-star starting point guard, went down with a shoulder injury which caused him to miss the remainder of the season. The Magic then began a stretch where they did not win or lose consecutive games for almost the entire month. The Magic did make a deal at the trade deadline with the Houston Rockets for Rafer Alston. Still having to deal with the absence of Nelson though, Orlando managed to maintain one of the top records in the league, secured a second straight winning season, and clinched a playoff berth in mid-March. The Magic defeated the defending world champion Boston Celtics to capture their second consecutive division championship, and on the same night assured themselves of winning more games than the previous season. Finishing the regular season with a 59–23 record, it was the most games the team had won in a season since the 1995–96 season in which they had 60 wins.
The Magic drew the Philadelphia 76ers in the first round of the playoffs. With the series tied at two wins for each team, Game 5 saw an incident in the 1st quarter involving Dwight Howard throwing an elbow at 76ers center Samuel Dalembert. Howard was assessed a technical foul but was not ejected from the game. The NBA reviewed the play and suspended Howard for Game 6. A second incident involving an elbow from Dwight Howard happened in Game 5 not long after the elbow to Dalembert. This time however, Magic rookie Courtney Lee was the recipient of the hit from his teammate. Lee left the game and did not return. Suffering a fractured sinus, it was announced that Lee was expected to have surgery and could miss the remainder of the postseason. Neither player's absence would prove costly to Orlando in Game 6, who won the series with a blowout on the road, and Lee returned to action in the next series wearing a protective face mask, such as one worn by Richard Hamilton.
In the Eastern Conference semifinals, the Magic faced the defending champion Boston Celtics. Facing a 3–2 series deficit, the Magic tied the series with a home game victory in Game 6 and advanced to the Eastern Conference Finals by winning Game 7 on the road, ending Boston's 32-0 undefeated record when leading the series 3-2. Assistant Coach Patrick Ewing had guaranteed a win in Game 7.
Returning to the conference finals for the first time since 1996, the Magic's opponent was the Cleveland Cavaliers, who compiled the league's best regular season record led by the season's MVP, LeBron James. That didn't stop the Magic as they closed the series out at home in Game 6, winning 103-90 as Dwight Howard scored 40 points, a career high for him in a playoff game. The Magic won the series 4-2, the Eastern Conference championship, and the right to face the Los Angeles Lakers in the 2009 NBA Finals.
After dropping the first two games in the series, the Magic finally won their first ever game in the finals in Game 3. With the franchise losing their first six finals games 1995 and 2009 combined, it was the second most games a team had lost in the finals before earning their first win. However, in Game 4 the Magic lost to the Lakers 99-91 in overtime; the Lakers took a 3-1 series lead and won again in Game 5, thus ending the Magic's longest playoff run in team history and ending up 1-8 in the Finals.