The 1998–99 NBA season was the Raptors' fourth season in the National Basketball Association. In the 1998 NBA draft, the Raptors selected Antawn Jamison out of the University of North Carolina with the fourth overall pick. However, they traded Jamison to the Golden State Warriors for his college teammate Vince Carter, who is also second-year star Tracy McGrady's cousin. Other offseason acquisitions included Charles Oakley from the New York Knicks, Kevin Willis from the Houston Rockets and free agent Michael Stewart. During the regular season, which was shortened due to a four-month lockout, the Raptors moved into their new arena Air Canada Centre. After a 6–12 start, the Raptors played their best basketball winning 12 of their next 14 games. However, they lost 13 of their final 18 games, and finished the season with a 23–27 record, sixth in the Central Division. Carter averaged 18.3 points per game and was named Rookie of the Year. Following the season, John Wallace re-signed as a free agent with the New York Knicks.

Carter was drafted by the NBA's Golden State Warriors 5th overall and then traded to the Toronto Raptors for Antawn Jamison, his UNC college teammate and best friend. Carter and Jamison played together at the University of North Carolina.

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