The 1998–99 NBA season was the Grizzlies' fourth season in the National Basketball Association. During the offseason, the Grizzlies signed free agent Cherokee Parks. After playing in 19 games, Sam Mack was traded back to the Houston Rockets midway through the season. In a lockout shortened season cut to 50 games, top draft pick Mike 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. However, a knee injury limited Bryant Reeves to just 25 games as the Grizzlies struggled again, posting a 13-game losing streak after a 4–6 start to the season. The Grizzlies lost their final seven games, returning to last place in the Midwest Division with a league worst record of 8–42. Following the season, Tony Massenburg was traded to the Houston Rockets.

The Grizzlies' first draft pick was Mike Bibby, which was the second overall pick in the draft.

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.

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