1999–2000 Detroit Pistons season

• Alvin Gentry (fired)
• George Irvine (lost to Heat 0–3)

The 1999–2000 Detroit Pistons season was the 52nd season for the Detroit Pistons in the National Basketball Association, and their 43rd season in Detroit, Michigan. During the off-season, the team re-signed free agents, and former Pistons players Terry Mills, and Michael Curry.

After the retirements of All-Star guard Joe Dumars and Bison Dele, the Pistons struggled losing their first four games of the regular season, but then won 18 of their next 28 games, and held a 25–23 record at the All-Star break. At mid-season, Don Reid was released to free agency, and later on signed with the Washington Wizards, while head coach Alvin Gentry was fired after a 28–30 start, and was replaced with assistant George Irvine. The Pistons won 14 of their next 24 games, and finished in fourth place in the Central Division with a 42–40 record, earning the seventh seed in the Eastern Conference.

Grant Hill averaged 25.8 points, 6.6 rebounds, 5.2 assists and 1.4 steals per game, and was named to the All-NBA Second Team, while Jerry Stackhouse averaged 23.6 points and 1.3 steals per game, and Lindsey Hunter provided the team with 12.7 points, 4.0 assists and 1.6 steals per game, and also led them with 168 three-point field goals. In addition, Christian Laettner provided with 12.2 points and 6.7 rebounds per game, while Jerome Williams played a sixth man role off the bench, averaging 8.4 points and 9.6 rebounds per game, Mills contributed 6.7 points and 4.8 rebounds per game, and Curry contributed 6.2 points per game off the bench.

During the NBA All-Star weekend at The Arena in Oakland in Oakland, California, Hill and Stackhouse were both selected for the 2000 NBA All-Star Game, as members of the Eastern Conference All-Star team; it was Stackhouse's first ever All-Star appearance. In addition, Hill also participated in the NBA 2Ball Competition, along with Jennifer Azzi of the WNBA's Detroit Shock, while Stackhouse participated in the NBA Slam Dunk Contest for the second time. Hill also finished in eighth place in Most Valuable Player voting, while Stackhouse finished in third place in Most Improved Player voting, and Williams finished in fifth place in Sixth Man of the Year voting.

In the Eastern Conference First Round of the 2000 NBA playoffs, the Pistons faced off against the 2nd–seeded, and Atlantic Division champion Miami Heat, who were led by All-Star center, and Defensive Player of the Year, Alonzo Mourning, and Jamal Mashburn; the Heat were without Tim Hardaway, who was out due to a knee injury. However, prior to the playoffs, Hill suffered a devastating ankle injury during the final month of the regular season, then re-injured his ankle during Game 2, in which the Heat defeated the Pistons, 84–82 at the American Airlines Arena to take a 2–0 series lead. Without Hill, the Pistons lost Game 3 to the Heat at home, 91–72 at The Palace of Auburn Hills, thus losing the series in a three-game sweep.

The Pistons finished 16th in the NBA in home-game attendance, with an attendance of 678,470 at The Palace of Auburn Hills during the regular season. Following the season, Hill was traded to the Orlando Magic after six seasons with the Pistons, while Hunter was traded to the Milwaukee Bucks, and Laettner and Mills were both dealt to the Dallas Mavericks, while Loy Vaught was traded to the Mavericks in a separate trade. However, Mills was released by the Mavericks, and signed as a free agent with the Indiana Pacers.

For the season, the Pistons added new dark red alternate road uniforms with black side panels, which would remain in use until 2001.