The 1999–2000 NBA season was the 30th season for the Portland Trail Blazers in the National Basketball Association.^[1] During the off-season, the Blazers acquired All-Star forward and 6-time champion Scottie Pippen from the Houston Rockets,^{[2][3][4][5][6]} acquired Steve Smith from the Atlanta Hawks,^{[7][8][9][10]} and signed free agent Detlef Schrempf.^{[11][10][12][13]} The Blazers got off to a fast start winning 13 of their first 15 games, 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.^[14] The 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.^[15] Finishing second in the Pacific Division, they earned the #3 seed in the Western Conference on the basis that the 55–27 Utah Jazz won the Midwest Division title. (However, the Blazers would enjoy the homecourt advantage over Utah in their second-round playoff series).^[16][17] The Blazers made the playoffs for the 18th consecutive year.^[18]

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,^{[19][20][21][22][23]} 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, and Brian Grant provided with 7.3 points and 5.5 rebounds per game,^[24] but only played 63 games due to knee and foot injuries.^[25][26]

In the playoffs, the Blazers defeated the Minnesota Timberwolves, 3–1 in the Western Conference First Round,^{[27][28][29][30]} and the 2nd-seeded Jazz, 4–1 in the Western Conference Semi-finals for the second consecutive year.^{[31][32][33][34]} In the Western Conference finals against the Los Angeles Lakers, the Blazers came back from a 3–1 series deficit to force Game 7.^[35][36] Up by 15 points with ten minutes remaining in Game 7, the Blazers suffered a 15–0 run by Los Angeles that tied the score, and the Lakers pulled out an 89–84 victory to advance to the 2000 NBA Finals,^{[37][38][39][40]} where they would go on to defeat the Indiana Pacers in six games to win their 12th NBA championship.^{[41][42][43][44][45]} Following the season, Grant was traded to the Miami Heat,^{[46][47][48][49]} and Jermaine O'Neal was dealt to the Indiana Pacers.^[50][51][52]

The 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 playoffs.^[53][54] The Blazers would not return to the Western Conference finals until 2019.

Although the Trail Blazers did not have any picks in the 1999 NBA draft, they were active during the offseason. On draft day, the Blazers purchased the draft rights to Roberto Bergersen from the Atlanta Hawks. Bergersen would not sign with the team; instead, he signed with the Idaho Stampede of the Continental Basketball Association. On August 2, the Blazers traded Jim Jackson and Isaiah Rider to the Hawks for Ed Gray and Steve Smith. The same day, the Blazers signed veteran forward Detlef Schrempf. Smith would be the starting shooting guard on the "Jail Blazers". Schrempf would finish his career with Portland, retiring in 2001.

On October 2, the Blazers were involved in a seven-player trade with the Houston Rockets. In the trade, the Blazers traded six players—Stacey Augmon, Kelvin Cato, Ed Gray, Carlos Rogers, Brian Shaw, and Walt Williams—for Scottie Pippen. Pippen would be the Blazers' starting small forward until 2003, when he signed with the Chicago Bulls, the team which he spent the majority of his career with. On October 5, the Blazers signed Antonio Harvey, and the following day, they signed Joe Kleine. On October 12, the Rockets waived Augmon, and the Blazers re-signed him on October 18.^[55]

The Blazers owned no picks in the 1999 NBA draft.

NOTE: Please write the players statistics in alphabetical order by last name.

• Rasheed Wallace, NBA All-Star
• Scottie Pippen, NBA All-Defensive Second Team