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 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, but they continued to struggle. In Bryan Colangelo's first year as President and General Manager, the first overall NBA draft selection of Andrea Bargnani and a revamp of the roster, helped the Raptors qualify for their first playoff berth in five years and capture the 2007 Atlantic Division title with 47 wins. In the 2007–08 season, they advanced to the playoffs again but failed to make the next four playoffs. 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.
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. Bosh and James eventually chose to converge in Miami with Wade, and the sign-and-trade transaction that ensued resulted in the Raptors receiving two first-round draft picks and a trade exception from Miami. Prior to this, Toronto had drafted Ed Davis, also a left-handed power forward like Bosh. After Bosh left, Colangelo sought to trade Calderón, Evans and the disenchanted Türkoğlu for Tyson Chandler, Leandro Barbosa, and Boris Diaw, but the trade involving Chandler collapsed at the last minute, as Chandler was traded to the Dallas Mavericks instead. Belinelli was then traded to New Orleans Hornets for Julian Wright, and 13 games into the season, Jack, David Andersen, and Marcus Banks to New Orleans for Peja Stojaković and Jerryd Bayless. Bosh's first return to Toronto was received to a chorus of boos, but not as nearly as harsh as what former Raptors Tracy McGrady and Vince Carter received upon their return. Toronto as a team regressed and were only able to secure 22 wins in the regular season.
Prior to the 2011–12 season, Dwane Casey, who was an assistant coach with the Dallas Mavericks, was officially hired as the new head coach on 21 June 2011. In the 2011 NBA Draft, the Raptors used their number five pick to select Jonas Valančiūnas, a centre from Lithuania. However, this season has been shortened, due the 2011 NBA lockout. NBA team owners and players later agreed to a new collective bargaining agreement to end the lockout, but it meant that 16 regular season games had to be cancelled, 8 of which were home games. The Raptors finished the season with a 23–43 record.
During the 2012 off-season, Colangelo worked hard to lure Canadian free agent and two-time MVP, Steve Nash, who became a free agent after playing for the Phoenix Suns, to play for the Raptors. Reports indicate that Nash was offered a three-year contract in excess of $30 million, but he turned this deal down, much to the disappointment of many Canadian basketball fans, as he turned to the Los Angeles Lakers instead. In lieu of Nash, the Raptors acquired point guard Kyle Lowry from the Houston Rockets for a future first round pick. Lowry, combined with the 2011 draft pick Jonas Valančiūnas and the 8th pick in the 2012 draft Terrence Ross, began the next phase of the re-building process. On 30 January 2013, the Raptors acquired Memphis Grizzlies star Rudy Gay and centre Hamed Haddadi in a three-way deal that sent José Calderón to the Detroit Pistons and Ed Davis, along with Pistons players Tayshaun Prince and Austin Daye and a 2nd round pick to the Grizzlies. Hamed Haddadi was later traded, along with a second round pick, to the Phoenix Suns, in exchange for guard Sebastian Telfair. The 2012–13 season was the first season since 2009 that the Raptors finished the season with a winning home record, despite their overall losing record.
Toronto Raptors Roster
|Rudy Gay||22||Small forward|
|Kyle Lowry||3||Point guard|
|Landry Fields||2||Shooting guard|
|Alan Anderson||6||Small forward|
|Sebastian Telfair||13||Point guard|
|Mickael Pietrus||20||Shooting guard|
|John Lucas 111||5||Point guard|
|Linas Kleiza||11||Small forward|