1999–2000 Cleveland Cavaliers season

The 1999–2000 NBA season was the 30th season for the Cleveland Cavaliers in the National Basketball Association. In the 1999 NBA draft, the Cavaliers selected point guard Andre Miller from the University of Utah with the eighth overall pick (which was acquired from the Boston Celtics), and also selected shooting guard Trajan Langdon out of Duke University with the eleventh overall pick. During the off-season, the team acquired Lamond Murray from the Los Angeles Clippers, and signed free agent Mark Bryant.

After only playing just five games the previous season, Zydrunas Ilgauskas would miss the entire regular season due to continuing foot injuries. Under new head coach Randy Wittman, the Cavaliers played around .500 basketball with an 11–9 start to the season, but then continued to struggle losing ten of their next eleven games, and held a 19–30 record at the All-Star break. The Cavaliers finished in sixth place in the Central Division with a 32–50 record.

Shawn Kemp led the team with 17.8 points, 8.8 rebounds and 1.2 blocks per game, while Murray averaged 15.9 points, 5.7 rebounds and 1.4 steals per game, and Bob Sura provided the team with 13.8 points and 3.9 assists per game, and also led them with 122 three-point field goals. In addition, Miller provided with 11.1 points and 5.8 assists per game, was named to the NBA All-Rookie First Team, while Brevin Knight contributed 9.3 points, 7.0 assists and 1.6 steals per game, and Wesley Person contributed 9.2 points per game and 106 three-point field goals. Meanwhile, Danny Ferry contributed 7.3 points per game off the bench, while on the defensive side, Andrew DeClercq averaged 6.6 points and 5.4 rebounds per game, and Bryant provided with 5.7 points and 4.7 rebounds per game.

Sura finished tied in eleventh place in Most Improved Player voting, and Miller finished in fourth place in Rookie of the Year voting.

Following the season, Kemp was traded to the Portland Trail Blazers in a three-team trade, while Sura was traded to the Golden State Warriors, DeClercq was dealt to the Orlando Magic, Bryant was released to free agency, and Ferry signed as a free agent with the San Antonio Spurs.

For the season, the Cavaliers changed their uniforms, which would remain in use until 2003.