The 1998–99 NBA season was the Grizzlies' fourth season in the National Basketball Association. The Grizzlies had the second pick in the 1998 NBA draft, which they used to select University of Arizona point guard Mike Bibby. During the offseason, the team signed free agent Cherokee Parks. In a lockout shortened season cut to 50 games, the Grizzlies had a 4–6 record in their first ten games, but then struggled posting a 13-game losing streak as a knee injury limited Bryant Reeves to just 25 games. Midway through the season, Sam Mack was traded back to the Houston Rockets. The Grizzlies lost their final seven games, returning to last place in the Midwest Division with a league worst record of 8–42. Bibby had a solid rookie season averaging 13.2 points and 6.5 assists per game, as he was named to the All-Rookie First Team. In addition, Shareef Abdur-Rahim continued to improve posting a career high of 23.0 points per game. Following the season, Tony Massenburg was traded to the Houston Rockets.
Due to the 1998–99 NBA lockout, the NBA would see a shortened schedule for the 1998–99 season, as every team would play 50 games, compared to 82 in a normal season. The Grizzlies began the season with their best start in franchise history, as they had a 3–3 record in their first six games, the latest in a season that the club had a .500 record. Vancouver would fall into a bad streak, losing sixteen of their next seventeen games, which included a thirteen-game losing streak, to fall out of the playoff picture. Wins would be few and far between for the remainder of the season, as the Grizzlies ended the year with a record of 8–42, which represented a .160 winning percentage, the lowest in team history. Vancouver finished with the worst record in the league for the third time in four seasons.
On February 16, 1999, Vancouver defeats the Los Angeles Clippers 93-89 in double overtime, to even their record to 3-3, the latest they had ever been .500 in a season. This would be their only road win of the season.
On February 23, 1999, Shareef Abdur-Rahim leads the Grizzlies with 28 points, as they stun the Los Angeles Lakers with a 93-83 victory, recording their first ever victory against the Lakers.