The 1998–99 NBA season was the Rockets' 32nd season in the National Basketball Association, and 28th season in Houston. To replace the retiring Clyde Drexler, the Rockets acquired All-Star forward Scottie Pippen from the Chicago Bulls after a four-month lockout. The team also signed free agent Antoine Carr, who appeared in two NBA Finals appearances with the Utah Jazz. With the addition of Pippen along with Hakeem Olajuwon and Charles Barkley, plus re-acquiring three-point specialist Sam Mack from the Vancouver Grizzlies at midseason, the Rockets played solid basketball posting a nine-game winning streak in March, and finished third in the Midwest Division with a 31–19 record. Pippen had a solid season averaging 14.5 points per game while rookies Michael Dickerson, and Cuttino Mobley were both selected to the All-Rookie Second Team. In the playoffs, the Rockets lost 3–1 in the first round to the Los Angeles Lakers.

Pippen spent only one season with the Rockets, and was traded to the Portland Trail Blazers before the following season. Also following the season, Dickerson and Carr were traded along with Othella Harrington, and Brent Price to the Vancouver Grizzlies, Mack and Matt Maloney were both released as Maloney would sign with the Chicago Bulls during the next season, and Eddie Johnson retired.

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