1999–2000 Portland Trail Blazers season

The 1999–2000 Portland Trail Blazers 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 NBA champion Scottie Pippen from the Houston Rockets, acquired Steve Smith from the Atlanta Hawks, and signed free agent Detlef Schrempf.

With the addition of Pippen, Smith and Schrempf, the Trail Blazers got off to a fast start by winning 13 of their first 15 games of the regular season, and later on held the league's best record at 38–11 before the All-Star break. The team posted an 11-game winning streak in February, but later on fell out of first place. The Trail Blazers 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 third seed in the Western Conference, and 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, 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. 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.

During the NBA All-Star weekend at The Arena in Oakland in Oakland, California, Wallace was selected for the 2000 NBA All-Star Game, as a member of the Western Conference All-Star team; it was his first ever All-Star appearance. Pippen finished tied in eighth place in Defensive Player of the Year voting.

In the Western Conference First Round of the 2000 NBA playoffs, the Trail Blazers faced off against the 6th–seeded Minnesota Timberwolves, a team that featured All-Star forward Kevin Garnett, Terrell Brandon, and rookie small forward Wally Szczerbiak. The Trail Blazers won the first two games over the Timberwolves at home at the Rose Garden Arena, before losing Game 3 on the road, 94–87 at the Target Center. The Trail Blazers won Game 4 over the Timberwolves on the road, 85–77 to win the series in four games.

In the Western Conference Semi-finals, and for the second consecutive year, the team faced off against the 2nd–seeded, and Midwest Division champion Utah Jazz, who were led by the trio of All-Star forward Karl Malone, All-Star guard John Stockton, and Bryon Russell. Despite the Jazz winning the Midwest Division title with a 55–27 record, the Trail Blazers had home-court advantage in the series. The Trail Blazers won the first three games over the Jazz to take a 3–0 series lead, but then lost Game 4 on the road, 88–85 at the Delta Center. The Trail Blazers won Game 5 over the Jazz at the Rose Garden Arena, 81–79 to win the series in five games.

In the Western Conference Finals, the Trail Blazers then faced off against the top–seeded, and Pacific Division champion Los Angeles Lakers, who were led by the trio of All-Star center, and Most Valuable Player of the Year, Shaquille O'Neal, All-Star guard Kobe Bryant, and Glen Rice. With the series tied at 1–1, the Trail Blazers lost the next two games to the Lakers at home, which included a Game 4 loss at the Rose Garden Arena, 103–91. However, the Trail Blazers came back from a 3–1 series deficit, and won the next two games over the Lakers, including a Game 6 win at home, 103–93 to even the series. In Game 7 at the Staples Center, the Trail Blazers were up by 15 points with ten minutes remaining in fourth quarter; however, the team then suffered a 15–0 run by the Lakers that tied the score, as the Trail Blazers lost the game, 89–84, thus losing in a hard-fought seven-game series. The Lakers would go on to defeat the Indiana Pacers in six games in the 2000 NBA Finals, winning their twelfth NBA championship.

The Trail Blazers finished third in the NBA in home-game attendance, with an attendance of 835,078 at the Rose Garden Arena during the regular season. 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 NBA playoff series until May 2, 2014, when Damian Lillard hit a three-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 the 2018–19 season.