The 1999-2000 season was the Detroit Pistons' 52nd season in the NBA and 43rd season in the city of Detroit. During the offseason, the Pistons re-signed free agents Terry Mills and Michael Curry. After the retirement of Joe Dumars, the Pistons were now led by Grant Hill and Jerry Stackhouse as they provided a 1-2 scoring punch and were both selected for the 2000 NBA All-Star Game. However, as the season wounded down, Hill suffered a devastating ankle injury. The Pistons went on to finish fourth in the Central Division with a 42–40 record. In the first round of the playoffs, they were swept by the Miami Heat in three straight games. Following the season, Hill was traded to the Orlando Magic, Lindsey Hunter was dealt to the Milwaukee Bucks, Christian Laettner was sent along with Loy Vaught to the Dallas Mavericks, and Mills signed as a free agent with the Indiana Pacers.

For the season, the Pistons added maroon alternate road uniforms which lasted until 2001.

(2) Miami Heat vs. (7) Detroit Pistons Last Playoff Meeting: Not available (first playoff series)