1998–99 Portland Trail Blazers season

The 1998–99 NBA season was the 29th season for the Portland Trail Blazers in the National Basketball Association. Due to a lockout, the regular season began on February 5, 1999, and was cut from 82 games to 50.

During the off-season, the Trail Blazers signed free agents Jim Jackson and Greg Anthony, who would reunite with his former University of Nevada, Las Vegas teammate Stacey Augmon, and acquired shooting guard, and top draft pick Bonzi Wells out of Ball State University from the Detroit Pistons, who selected him with the eleventh overall pick in the 1998 NBA draft. The Trail Blazers got off to a fast start by winning eight straight games between February and March, on their way to a 27–6 start to the regular season. Despite losing four of their final five games of the season, the team finished in first place in the Pacific Division with a 35–15 record, and earned the #2 seed in the Western Conference. The Trail Blazers won their fourth Division title in franchise history, and their first since the 1991–92 season; the team also qualified for their 17th consecutive trip to the NBA playoffs, and 22nd in 23 years.

Isaiah Rider led the team in scoring with 13.9 points per game, which is usually a low average in points for a team's scoring leader, while Rasheed Wallace played half the season off the bench, averaging 12.8 points per game, and Damon Stoudamire contributed 12.6 points and 6.2 assists per game. In addition, Brian Grant averaged 11.5 points and 9.8 rebounds per game, while Arvydas Sabonis provided the team with 12.1 points and 7.9 rebounds per game, Walt Williams contributed 9.3 points per game, and Jackson provided with 8.4 points per game off the bench. Head coach Mike Dunleavy was named the NBA Coach of the Year, and Wallace finished in second place in Sixth Man of the Year voting.

In the 1999 NBA playoffs, the Trail Blazers swept the Phoenix Suns in the Western Conference First Round in three straight games, marking the first time since 1992 that the team advanced to the playoffs. The Trail Blazers then defeated the 2-time defending Western Conference champion Utah Jazz in the Western Conference Semi-finals, four games to two, but were swept out of the Western Conference Finals by Tim Duncan, and the eventual NBA champion San Antonio Spurs in four straight games. The Spurs would reach the NBA Finals for the first time to defeat the 8th-seeded New York Knicks in five games, winning their first ever championship.

Following the season, Rider and Jackson were both traded to the Atlanta Hawks, and Williams and second-year center Kelvin Cato were both traded to the Houston Rockets.