1999–2000 Portland Trail Blazers season

The 1999–2000 NBA season was the 30th season for the Portland Trail Blazers in the National Basketball Association. During the off-season, the Trail Blazers acquired All-Star forward and 6-time champion Scottie Pippen from the Houston Rockets, acquired Steve Smith from the Atlanta Hawks, and signed free agent Detlef Schrempf.

The Trail Blazers got off to a fast start by winning 13 of their first 15 games of the regular season, then later on posted an 11-game winning streak in February, and held the league's best record with a 38–11 record at the All-Star break. The team finished with the second-best record in the league with a 59–23 record, which tied them for the second-highest win percentage in franchise history. Finishing in second place in the Pacific Division, the Trail Blazers earned the #3 seed in the Western Conference, on the basis that the Utah Jazz, who finished with a 55–27 record, won the Midwest Division title, (however, the Trail Blazers would enjoy the home-court advantage over the Jazz in their second-round playoff series). The Trail Blazers qualified for the NBA playoffs for the 18th consecutive year.

Rasheed Wallace averaged 16.4 points, 7.0 rebounds and 1.3 blocks per game, and was selected for the 2000 NBA All-Star Game in Oakland, California, which was his first All-Star appearance, while Smith finished second on the team in scoring averaging 14.9 points per game, and Pippen averaged 12.5 points, 6.3 rebounds, 5.0 assists and 1.4 steals per game, and was named to the NBA All-Defensive Second Team, and also finished tied in eighth place in Defensive Player of the Year voting. In addition, Damon Stoudamire provided the team with 12.5 points and 5.2 assists per game, and Arvydas Sabonis contributed 11.8 points and 7.8 rebounds per game. Off the bench, second-year guard Bonzi Wells contributed 8.8 points per game, while Schrempf averaged 7.5 points and 4.3 rebounds per game, Brian Grant provided with 7.3 points and 5.5 rebounds per game, but only played 63 games due to knee and foot injuries, and Greg Anthony contributed 6.3 points and 2.5 assists per game.

In the 2000 NBA playoffs, the Trail Blazers defeated the Minnesota Timberwolves, 3–1 in the Western Conference First Round, and the 2nd-seeded Jazz, 4–1 in the Western Conference Semi-finals for the second consecutive year. In the Western Conference Finals against the top-seeded Los Angeles Lakers, the Trail Blazers came back from a 3–1 series deficit to force Game 7; up by 15 points with ten minutes remaining in Game 7 at the Staples Center, the Trail Blazers suffered a 15–0 run by the Lakers that tied the score, and the Lakers pulled out an 89–84 victory to advance to the 2000 NBA Finals, where they would go on to defeat the Indiana Pacers in six games to win their twelfth NBA championship.

Following the season, Grant was traded to the Miami Heat in a three-team trade, and Jermaine O'Neal was dealt to the Indiana Pacers.

The Trail Blazers did not win another playoff series until May 2, 2014, when Damian Lillard hit a 3-point shot with 0.9 seconds left to beat the Houston Rockets 99–98 in Game 6 of the Western Conference First Round of the 2014 NBA playoffs. The Trail Blazers would not return to the Western Conference Finals again until 2019.