1999–2000 Toronto Raptors season

The 1999–2000 NBA season was the fifth season for the Toronto Raptors in the National Basketball Association. In the 1999 NBA draft, the Raptors received the fifth overall pick in a trade with the Denver Nuggets, and selected small forward, and high school basketball star Jonathan Bender, and also selected center, and Bosnian basketball star Aleksandar Radojević out of Barton Community College with the twelfth overall pick; the team soon traded Bender to the Indiana Pacers in exchange for Antonio Davis, and signed free agents Muggsy Bogues, and three-point specialist Dell Curry during the off-season.

However, Radojević only played just three games with the Raptors due to a left knee injury; Radojević played in the team's season opener at home against the Boston Celtics, and in the team's final two games of the regular season on the road, against the Miami Heat and the Orlando Magic.

In their first full season playing at the Air Canada Centre, the Raptors got off to a 12–6 start to the regular season, but then lost five of their next six games. However, the team got better as the season progressed, winning seven straight games between February and March, and holding a 26–21 record at the All-Star break. At mid-season, the team traded Alvin Williams to the Celtics in exchange for Danny Fortson, but the trade was voided due to Williams failing his physical exam; Williams only played 55 games this season due to knee injuries. The Raptors showed improvement as they finished in third place in the Central Division with a 45–37 record, earned the #6 seed in the Eastern Conference, and qualified for their first ever NBA playoff appearance.

Second-year star Vince Carter averaged 25.7 points, 5.8 rebounds and 1.3 steals per game, and was named to the All-NBA Third Team; he also won the NBA Slam Dunk Contest during the NBA All-Star weekend in Oakland, California, and was selected for the 2000 NBA All-Star Game, which was his first ever All-Star appearance. In addition, Tracy McGrady averaged 15.4 points, 6.3 rebounds and 1.9 blocks per game, while Doug Christie contributed 12.4 points, 4.4 assists and 1.4 steals per game, and Davis provided the team with 11.5 points, 8.8 rebounds and 1.3 blocks per game. Meanwhile Kevin Willis provided with 7.6 points and 6.1 rebounds per game off the bench, and Charles Oakley contributed 6.8 points and 6.9 rebounds per game.

Carter also finished in tenth place in Most Valuable Player voting, while McGrady finished tied in third place in Sixth Man of the Year voting, and in fifth place in Most Improved Player voting, and head coach Butch Carter finished tied in fifth place in Coach of the Year voting.

However, in the 2000 NBA playoffs, the Raptors were swept in the Eastern Conference First Round by the New York Knicks in three straight games. Following the season, McGrady was traded to the Orlando Magic, while Christie was dealt to the Sacramento Kings, Dee Brown signed as a free agent with the Magic, and Butch Carter was fired as head coach.

Butch 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 star Percy 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 University, Bobby Knight, had launched into a racist tirade during practice, which Knight denied.

Carter was involved in public feuds with Vince Carter and McGrady, limiting their minutes because he did not 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 NBA playoffs against the Knicks, Knicks center and former Raptors player Marcus Camby, who had played under Carter during the second half of 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 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.

This season saw the Raptors change their uniforms, adding side panels to their jerseys and shorts. The home jerseys remained in use until 2006, while the road jerseys lasted until 2003, where the city name "Toronto" was replaced with the team name "Raptors" on the front of their jerseys.