In the 1997–1998 season, Carter served as an assistant coach for the Toronto Raptors under Darrell Walker. He was promoted to the head coach position mid-way through the 1997–1998 season after Walker led the team to a franchise low (11-38) record. Carter finished the remainder of the season with a (5-28) record. During the shortened 1998-99 NBA season, Carter coached the Raptors to a (23-27) record, improving the team's winning percentage by .308 from the all-time franchise low (16-66) season. The second year also brought upon talent and scoring power from NBA All-Star Vince Carter, who played his rookie year on Carter's roster. In the 1999-2000 season, Carter coached the Raptors to their first winning season, with a (45 - 37) record, resulting in the team's first playoff appearance. Carter's turnaround of the Raptors from a franchise-worst dismal (16-66) record to a (45-37) record and a playoff berth in two and a half seasons was a great success. However, the playoff berth was short lived as the Raptors were eliminated in the first round by the Knicks.