Like most expansion teams, the Raptors struggled in their early years, but after the acquisition of Vince Carter through a draft day trade in 1998, the team set league-attendance records and made the NBA playoffs in 2000, 2001, and 2002. Carter was instrumental in leading the team to a then-franchise high 47 wins and their first playoff series win in 2001, where they advanced to the Eastern Conference semifinals. During the 2002–03 and 2003–04 seasons, they failed to make significant progress and he was traded in 2004 to the New Jersey Nets.
After Carter left, Chris Bosh emerged as the team leader. In 2006–07, Bryan Colangelo's first full season as President and General Manager, a combination of Bosh, 2006 first overall NBA draft pick Andrea Bargnani and a revamp of the roster helped the Raptors qualify for their first playoff berth in five years, capturing the Atlantic Division title with 47 wins. In the 2007–08 season, they advanced to the playoffs again, but failed to make the playoffs in each of the next five seasons. In a bid to persuade Bosh to stay, Colangelo overhauled the team roster for the 2009–10 season, but Bosh signed with the Miami Heat in July 2010, ushering in yet another era of rebuilding for the Raptors.
After Masai Ujiri was brought in as the new General Manager in 2013, he traded Bargnani to the New York Knicks. With a backcourt led by Kyle Lowry and DeMar DeRozan, the Raptors returned to the playoffs, won their second Atlantic Division title, and won a then-franchise record 48 games in the 2013–14 season. However, they failed for a fourth consecutive time to advance beyond the first round of the playoffs. In the 2014–15 season, they won a then-franchise record 49 games, but failed for a second consecutive year to advance past the first round of the playoffs, getting swept by the Washington Wizards, 4–0. In the 2015–16 season, they won a franchise record 56 games, finishing in second place in the conference for the first time in franchise history. In the playoffs, they won their first playoff series since 2001 by defeating both the Indiana Pacers and Miami Heat, advancing to the Conference Finals for the first time against the eventual champions Cleveland Cavaliers. However, the Raptors lost to the Cavaliers in six games.
The New Jersey/Brooklyn Nets and the Raptors have been minor rivals since the trade of Vince Carter to the Nets during the 2004–05 season. The rivalry began to heat up as the two teams faced each other in the opening round of the 2007 NBA Playoffs, with the Nets winning the series 4–2 after a go-ahead shot by Richard Jefferson with 8 seconds left in Game 6 ensuring 98–97 defeat for the Raptors. The rivalry was rekindled during the 2013–14 season when the Nets and Raptors battled for the Atlantic Division. The Raptors won the division final but then they found themselves facing the Nets in the opening round of the 2014 NBA Playoffs. Prior to Game 1 of the series, Raptors GM Masai Ujiri spoke at a Raptors rally outside Air Canada Centre's Maple Leaf Square. During the rally, Ujiri yelled "Fuck Brooklyn!" which found its way quickly onto social media platforms within minutes. Masai was fined $25,000 by the NBA for the quote and later apologized for the excessive language. The hard fought series lasted seven games, and was decided in the final seconds when Paul Pierce blocked Kyle Lowry's shot giving the Nets the 104–103 victory.
The New York Knicks and the Raptors had a playoff rivalry in 2000 and 2001. The Raptors made their first-ever playoff appearance during the 1999–2000 season, in which they were swept by the Knicks in the first round 3–0. The following season, the Raptors redeemed themselves, defeating the Knicks in the first round 3–2; this effectively ended the Knicks' run as perennial NBA championship contenders, which began in the early 1990s.
The Raptors Foundation was the charitable arm of the Raptors, dedicated to assisting Ontario's registered charities that support programs and sports initiatives for at-risk children and youth. The Foundation strove to lift spirits and change lives for young people by supporting local and provincial organizations that provide recreational, educational and other youth-oriented activities. Through its community ties and with the help of its corporate partners, donors, Raptors players and volunteers, the Foundation has successfully raised more than $14 million between 1995 and 2007, and reached out to thousands of other charities.[ The Raptors Foundation was one of three parts of the Raptors' community service program. The other projects are Raptors Community Relations and Raptors Basketball Development, both of which focus on providing basketball development programs. The Toronto Raptors lead the NBA for amount of money donated to the community. In 2009, the Raptors Foundation merged with the other charitable arms of MLSE's other sports franchises to form the Team Up Foundation.
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