As with 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 franchise set league-attendance records and made the NBA playoffs in 2000, 2001, and 2002.

For the 2006–07 season, Bryan Colangelo was appointed as general manager, and through a combination of Bosh, 2006 first overall draft pick Andrea Bargnani, and a revamp of the roster, the Raptors qualified for their first playoff berth in five years, capturing the Atlantic Division title.

[12] The team originally competed in the Central Division,[26] and before the inaugural season began, sales of Raptors merchandise ranked seventh in the league, marking a successful return of professional basketball to Canada.

[27] Thomas then selected a wide range of players in the expansion draft, including veterans Jerome Kersey, Willie Anderson and his former Pistons teammate John Salley.

[12] However, the selection of Stoudamire was met with boos from fans at the 1995 NBA draft at the SkyDome in Toronto, many of whom wanted Ed O'Bannon of UCLA, an NCAA Final Four Most Valuable Player.

[42] Anderson refused to report to Toronto and was traded to the Celtics with Žan Tabak and Popeye Jones for Chauncey Billups, Dee Brown, Roy Rogers and John Thomas.

[49][50][51] During the 1998 NBA draft, in what became a defining move for the franchise, Grunwald traded the team's fourth overall pick Antawn Jamison to the Golden State Warriors for Vince Carter, who was selected fifth overall, and cash.

Kevin Willis, another veteran acquired from the trade, solidified the centre position, while the coaching staff temporarily rotated Brown, Williams and Doug Christie to play point guard.

[67] With 10.7 seconds left in the game, and the Raptors down 85–82 with possession of the ball, Childs raced down the court and shot a three-pointer that missed badly, apparently trying to draw a foul on the play,[70] instead of passing to a wide-open Curry.

"[77] Rob Babcock was named general manager on June 7, 2004, alongside the appointments of Wayne Embry as senior advisor and Alex English as director of player development.

[105] Toronto ended the regular season with a 47–35 record, securing the third seed in the Eastern Conference for the 2007 NBA playoffs along with the Atlantic Division title, as well as homecourt advantage for the first time in franchise history.

Most notably, the Raptors acquired Carlos Delfino in a trade with Detroit for two second-round draft picks,[116] and signed Jamario Moon[117] and three-point specialist Jason Kapono as free agents.

However, Jameer Nelson, Rashard Lewis and Keith Bogans keyed strong three-point shooting in Game 4 and overcame Bosh's 39 points and 15 rebounds to bring the Magic out of Toronto with a 3–1 lead.

[123] As it turned out, a blockbuster trade was agreed in principle before the 2008–09 campaign: six-time All-Star Jermaine O'Neal was acquired from the Indiana Pacers in exchange for Ford (who had become expendable with the emergence of Calderón), Rasho Nesterović, Maceo Baston, and Roy Hibbert, the 17th pick in the 2008 NBA draft, giving the Raptors a potential boost in the frontcourt.

O'Neal and Moon were then traded to Miami for Shawn Marion and Marcus Banks,[127] but with the losses mounting, the Raptors soon fell out of the playoffs picture and were eliminated from contention with seven games of the regular season remaining.

[132] This was followed by the signing of free agent Hedo Türkoğlu, which in turn led to a sign-and-trade agreement involving four teams, with Toronto landing wing players Devean George (later traded for Marco Belinelli) and Antoine Wright, while releasing Marion, Kris Humphries and Nathan Jawai.

[133] Around the same time, Parker headed for the Cleveland Cavaliers,[134] while Indiana point guard Jarrett Jack was added and Nesterovič brought back to provide cover for the big men.

[76] However, a season-ending injury to Bosh after the break coincided with Toronto's descent down the standings from the fifth seed to the eighth, and they ultimately relinquished their spot to Chicago a few games before the regular season ended.

[138] Before the 2010–11 season began, there was much anticipation around the league over the fates of an elite pack of free agents, featuring the likes of Bosh, Dwyane Wade, LeBron James, and Amar'e Stoudemire.

On December 9, 2013, the Raptors traded Rudy Gay, Quincy Acy, and Aaron Gray to the Sacramento Kings for John Salmons, Greivis Vásquez, Patrick Patterson, and Chuck Hayes, and waived Augustin.

The Raptors, who were one of the four teams that never reached the NBA Conference Finals in their histories, appeared in the third round for the first time in their twenty-first season, facing the Cleveland Cavaliers,[159] in which they ultimately lost the series 4–2.

On January 1, 2018, DeMar DeRozan scored a franchise-record 52 points to help the Raptors beat the Milwaukee Bucks 131–127 in overtime, matching the team record with their 12th consecutive home victory.

First, on July 18, DeRozan was traded, along with Jakob Pöltl and a protected 2019 first-round draft pick, to the San Antonio Spurs in exchange for Kawhi Leonard and Danny Green.

After losing the first two games in Milwaukee, Toronto won the next four, advancing to the NBA Finals for the first time in franchise history, and their opponents were the two-time defending champions Golden State Warriors.

[189][190] They did not play again until March 3, but with five players missing due to the safety protocols, including Siakam, Anunoby, Lowry and Fred VanVleet, as well as head coach Nurse, resulting the Raptors to tank, Toronto lost 129–105 to the Detroit Pistons.

The team said in a press release that the new uniform designs were intended to pay tribute to the city of Toronto and to Canada as a whole, noting that the Raptors were the sole Canadian club in the NBA since the Grizzlies' move to Memphis.

Nine Raptors have been selected to play in the All-Star game: Vince Carter, Antonio Davis, Chris Bosh, DeMar DeRozan, Kyle Lowry, Kawhi Leonard, Pascal Siakam, Fred VanVleet and Scottie Barnes.

MLSE decided to endorse this practice by setting up concession stands and branded sponsorships at the square with naming rights sold to Ford Motor Company's Canadian operations, along with increased security.

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.

[255] 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 a 98–97 defeat for the Raptors.