1999–2000 Milwaukee Bucks season

The 1999–2000 Milwaukee Bucks season was the 32nd season for the Milwaukee Bucks in the National Basketball Association. During the off-season, the team acquired Danny Manning and re-acquired Dale Ellis from the Orlando Magic, and signed free agents Darvin Ham and J.R. Reid.

With Sam Cassell playing a full season after dealing with an ankle injury the previous season, the Bucks got off to a 14–10 start to the regular season, and later on held a 26–24 record at the All-Star break. At mid-season, the team traded Ellis to the Charlotte Hornets, while Haywoode Workman was released to free agency, and signed with the Toronto Raptors. The Bucks struggled losing nine of their twelve games in February, as the team fell below .500 in winning percentage, and later on held a 32–37 record as of March 24, 2000. However, the Bucks managed to win 10 of their final 13 games of the season, finishing in fifth place in the Central Division with a 42–40 record, and earning the eighth seed in the Eastern Conference.

Ray Allen averaged 22.1 points, 3.8 assists and 1.3 steals per game, and led the Bucks with 172 three-point field goals, while Glenn Robinson averaged 20.9 points and 6.0 rebounds per game, and Cassell provided the team with 18.2 points, 9.0 assists and 1.3 steals per game. In addition, Tim Thomas played a sixth man role off the bench, averaging 11.8 points and 4.2 rebounds per game, while Scott Williams provided with 7.6 points and 6.6 rebounds per game, Vinny Del Negro contributed 5.2 points per game, Ervin Johnson averaged 4.8 points, 8.1 rebounds and 1.6 blocks per game, and Manning contributed 4.6 points and 2.9 rebounds per game.

During the NBA All-Star weekend at The Arena in Oakland in Oakland, California, Allen and Robinson were both selected for the 2000 NBA All-Star Game, as members of the Eastern Conference All-Star team; it was the first ever All-Star appearance for both players. In addition, Allen also participated in the NBA Three-Point Shootout.

In the Eastern Conference First Round of the 2000 NBA playoffs, and for the second consecutive year, the Bucks faced off against the top–seeded, and Central Division champion Indiana Pacers, who were led by Most Improved Player of the Year, Jalen Rose, All-Star guard Reggie Miller, and All-Star forward Dale Davis. After trailing 2–1 in the series, the Bucks won Game 4 over the Pacers at home, 100–87 at the Bradley Center to even the series. However, the Bucks lost Game 5 to the Pacers on the road, 96–95 at the Conseco Fieldhouse, thus losing in a hard-fought five-game series. The Pacers would advance to the NBA Finals for the first time in franchise history, but would lose to the Los Angeles Lakers in six games in the 2000 NBA Finals.

The Bucks finished 19th in the NBA in home-game attendance, with an attendance of 628,605 at the Bradley Center during the regular season. Following the season, Manning signed as a free agent with the Utah Jazz, while in a three-team trade, Del Negro was traded to the Golden State Warriors, and Reid and second-year forward Robert Traylor were both dealt to the Cleveland Cavaliers.