Prior to the 1999–2000 season, Portland acquired veteran all-star Scottie Pippen, and coach Mike Dunleavy decided to use Grant as a reserve behind rising all-star Rasheed Wallace, who would go on to have a career year during the season as the Trail Blazers won 59 games and the second seed in the Western Conference. Portland opened the playoffs with a 3-1 first-round win over the Minnesota Timberwolves, with Grant and Wallace both being used as defensive options against Kevin Garnett. Grant was used in a similar fashion against Karl Malone and the Utah Jazz in the second round, with Portland advancing in five games. In the Western Conference Finals, the Trail Blazers faced the Los Angeles Lakers led by Pippen's former Chicago Bulls coach Phil Jackson and the duo of Shaquille O'Neal and Kobe Bryant. The teams split the first two games before the Lakers took games 3 and 4 to take a 3–1 series lead, but Portland responded with a win on the road in game 5 and a home win in the sixth game to set up a seventh game with a trip to the NBA Finals on the line. Despite taking a double-digit lead into the fourth quarter, the Lakers rallied and won the game, eliminating Portland. Grant averaged 5.4 points and 5.8 rebounds throughout the 2000 playoff run.