The 1989-90 season was the 20th season for the Portland Trail Blazers in the National Basketball Association (NBA), in which the Blazers finished with a franchise-high 59–23 record and returned to the NBA Finals for the first time since their championship season of 1976–77. However, they were unsuccessful in capturing their second NBA title, as they fell to the Detroit Pistons four games to one.
Clyde Drexler continued to be the leading scorer for the Trail Blazers with 23.3 ppg, as the Blazers rebounded off their disappointing season to post a solid 59-23 record good enough for second place in the Pacific, as the Blazers were made stronger by acquiring Buck Williams, a 6-8 rebounding machine from the New Jersey Nets for Sam Bowie. The acquisition of Williams helped make the Blazers stronger for the playoffs and it showed as they won their first playoff series in five years by sweeping the Dallas Mavericks in three straight games. In the second round the Blazers needed seven games to get past the San Antonio Spurs as the home team won all seven games. In the Western Conference Finals the Trail Blazers continued to defend their home court well, jumping out to a 2-0 lead over the Phoenix Suns. The Suns rebounded to take the next two in Phoenix as the Blazers won Game 5 at home 120-114. However, there would be no need for a seventh game as the Blazers knocked off the Suns with a 112-109 win in Game 6 to reach the NBA Finals for the second time in franchise history. In the Finals the Trail Blazers got off to a solid start, splitting the first two games on the road against the defending NBA Champion Detroit Pistons. However, the Blazers dropped all three games at home as the Pistons won the NBA title in five games.
During the season, Dražen Petrović won the Euroscar Award, presented by the Italian basketball magazine Superbasket to the top player in Europe. Unlike major NBA awards, the Euroscar is awarded for a player's performance during a calendar year, and also takes into account a player's performances for his national team. In Petrović's case, the award considered his performances in 1989 for Real Madrid and the Yugoslavia national team, as well as the Blazers. This was the second of what would eventually be four Euroscars for Petrović.