The 1999–2000 NBA season was the Raptors' fifth season in the National Basketball Association. During the offseason, the Raptors acquired Antonio Davis from the Indiana Pacers, and signed free agentsMuggsy Bogues and three-point specialist Dell Curry. In their first full season playing at the Air Canada Centre, the Raptors got better as the season progressed. Second-year star Vince Carter led the team in scoring, averaging 25.7 points per game. He also won the Slam Dunk Contest in Oakland and was selected for the 2000 NBA All-Star Game. The Raptors improved and qualified for their first playoff appearance with a 45–37 record, finishing third in the Central Division. However, in the postseason, they were swept in the first round by the New York Knicks in three straight games. Following the season, Tracy McGrady signed with the Orlando Magic, Doug Christie was dealt to the Sacramento Kings, Dee Brown signed as a free agent with the Magic, and head coach Butch Carter was fired. Carter was fired on June 13, 2000 after the organization decided they wanted a return of "stability" to the franchise. In his last season as coach of the Raptors, he invited friend and rap starPercy Miller, otherwise known as Master P, to the pre-season training camp to try out for the team. Carter claimed it was an attempt to deflect media attention away from Vince Carter, but was criticized for trying to draw attention to himself and his friendship with Miller. Carter also released a book where he claimed that his coach at Indiana, Bobby Knight, had launched into a racist tirade during practice, which Knight denied. Carter was involved in public feuds with stars Vince Carter and Tracy McGrady, limiting their minutes because he didn't want to burn them out in their young careers. Carter also had an off-court feud with his ex-wife. During the opening round of the 2000 NBA Playoffs against the Knicks, Knick center Marcus Camby, who had played under Carter during the 1997–98 season, made what Carter considered an inflammatory remark about Carter by calling him a "liar", and Carter decided to file a $5-million defamation suit against him for what he said were inaccurate statements. NBA Deputy Commissioner Russ Granik believed it was a frivolous suit and criticized Carter for filing it, which led to Carter dropping the suit. In his last few weeks as Raptors coach, Butch Carter made attempts to ouster friend Glen Grunwald as General Manager and was cited as one of the reasons why Tracy McGrady decided to leave the team and sign with the Orlando Magic. The Raptors organization, players, and fans all had decided that Carter's off-court issues were too much of a distraction for the team going forward. The season saw the Raptors change their uniforms which lasted until 2006.
Vince Carter was selected to an All-Star Team for the first time, and showcased his athleticism and dunking abilities in the 2000 NBA Slam Dunk Contest. He won the contest by performing an array of dunks including a 360° windmill, a between the legs, and an "elbow dunk." Though he has not competed in the dunk contest since, Carter has been voted into the Eastern Conference NBA All-Star Team starting lineup several times through fan balloting.