The 1999–2000 NBA season was the 30th season of the National Basketball Association in Cleveland, Ohio. During the offseason, the Cavaliers acquired Lamond Murray from the Los Angeles Clippers. Under new head coach Randy Wittman, the Cavaliers played around .500 with a 11–9 record in their first 20 games, but then continued to struggle without Zydrunas Ilgauskas, who missed the entire season due to foot injures. The team finished 6th in the Central Division with a 32–50 record. Shawn Kemp led the team in scoring, rebounds and blocks, and top draft pick Andre Miller made the All-Rookie First Team. The Cavaliers also finished the season with the highest amount of defensive 3-second violations, a record that still stands today. Following the season, Kemp was traded to the Portland Trail Blazers, Bob Sura was traded to the Golden State Warriors, Andrew DeClercq was dealt to the Orlando Magic, and Danny Ferry signed as a free agent with the San Antonio Spurs.

For the season, the Cavaliers changed their uniforms which would last until 2003.

^*1st round pick acquired from Boston in Vitaly Potapenko deal.