The 1999–2000 NBA season was the 54th season for the Boston Celtics in the National Basketball Association. During the offseason, the Celtics signed free agent Calbert Cheaney while acquiring Danny Fortson, and former Celtics forward Eric Williams from the Denver Nuggets. In the third year of the Rick Pitino era, the Celtics played around .500 for the first few months, but then suffered a ten-game losing streak between March and April. Fans and the media began to show their impatience with the struggling franchise, who finished out of the playoffs again with a 35–47 record, fifth in the Atlantic Division. Second-year star Paul Pierce had a stellar season averaging 19.5 points per game. Following the season, Dana Barros was traded to the Dallas Mavericks, who then traded him to the Detroit Pistons two months later, Cheaney was traded to the Denver Nuggets, and Fortson was dealt to the Golden State Warriors.

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