The 1999–2000 NBA season was the Timberwolves' 11th season in the National Basketball Association. For the season opener, the Timberwolves traveled to Tokyo, Japan to play their first two games against the Sacramento Kings. Despite posting an 8-game losing streak in December, the Timberwolves enjoyed their first 50-win season finishing third in the Midwest Division with a 50–32 record. Superstar forward Kevin Garnett led the way averaging 22.9 points, 11.8 rebounds and 5.0 assists per game, while being selected for the 2000 NBA All-Star Game. Top draft pick Wally Szczerbiak had a solid rookie season finishing third on the team in scoring with 11.6 points per game, and made the All-Rookie First Team. However, in the first round of the playoffs, they lost in four games to the Portland Trail Blazers. Following the season, tragedy struck as Malik Sealy died in an automobile accident on May 20, 2000. Also following the season, Bobby Jackson signed as a free agent with the Sacramento Kings.

(3) Portland Trail Blazers vs. (6) Minnesota Timberwolves Last Playoff Meeting: Not available (first playoff series)

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