The 1999–2000 NBA season was the Bulls' 34th season in the National Basketball Association. The Bulls won the Draft Lottery, and selected Elton Brand out of Duke University with the first pick in the 1999 NBA draft. Offseason acquisitions included acquiring Hersey Hawkins from the Seattle SuperSonics, and re-signing free agents B.J. Armstrong and Will Perdue, who both won championships with the team in the early 1990s. However, the Bulls struggles continued as they lost 26 of their first 28 games. At midseason, Toni Kukoč was traded to the Philadelphia 76ers, as the team acquired John Starks from the Golden State Warriors in a three-team trade. However, after just four games, Starks was released to free agency.

The Bulls finished last place in the Central Division with a 17–65 record. Brand averaged 20.1 points, 10.0 rebounds and 1.6 blocks per game. He was named Rookie of The Year along with Steve Francis of the Houston Rockets. First round draft pick Ron Artest was named to the All-Rookie Second Team. Following the season, Hawkins re-signed as a free agent with the Charlotte Hornets, Randy Brown signed with the Boston Celtics, and Armstrong retired while Perdue was released.

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