The 1998–99 NBA season was the 76ers 50th season in the NBA and 36th season in Philadelphia. After a four-month lockout wiped out half the season, the Sixers signed free agents Matt Geiger and George Lynch during the offseason, and traded Tim Thomas and Scott Williams to the Milwaukee Bucks for Tyrone Hill at midseason. The Sixers recorded their first winning month in five years, on their way to making the playoffs for the first time in eight years with a 28–22 record, third in the Atlantic Division. Allen Iverson led the league in scoring averaging 26.8 points per game. In the first round of the playoffs, the Sixers defeated the 3rd–seeded Orlando Magic in four games, but were swept in the semifinals by the Indiana Pacers in four straight games. Following the season, Rick Mahorn retired after making his second stint with the Sixers.

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

Last Playoff Meeting: This is the first meeting between the Magic and 76ers.

(2) Indiana Pacers vs. (6) Philadelphia 76ers: Pacers win series 4-0

Last Playoff Meeting: 1981 Eastern Conference First Round (Philadelphia won 2-0)

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