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. During the offseason, the Blazers signed free agents Jim Jackson and Greg Anthony, who would reunite with his former UNLV teammate Stacey Augmon. Portland got off to a fast start winning 15 of their first 18 games, and went 35–15 in the lockout-shortened season, earning their fourth Pacific Division title and the first since 1991–92. Their record qualified them for the #2 seed in the Western Conference. The team earned their 17th straight trip to the playoffs, and 22nd in 23 years. Head coach Mike Dunleavy was named Coach of The Year.

The Blazers swept the Phoenix Suns in the first round in three straight games, marking the first time since 1992 that the Blazers advanced in the playoffs. They followed with a 4–2 series victory over the two-time defending Western Conference champion Utah Jazz, but were swept out of the Western Conference Finals by the eventual NBA champion San Antonio Spurs in four straight games. Following the season, Jackson and Isaiah Rider were traded to the Atlanta Hawks, and Walt Williams and second-year center Kelvin Cato were traded to the Houston Rockets.

The Blazers owned no picks in the 1998 NBA draft.