Preseason

The Raptors entered the 2009–10 NBA season in a state of flux: they had failed to qualify for the 2009 NBA Playoffs; it was Jay Triano's first full season in charge; and there was much uncertainty over the futures of perennial All-Star and captain Chris Bosh (who was into the final year of his contract), as well as Shawn Marion and Anthony Parker, both of whom could possibly become free agents before the season began. The roster shakeup began on 9 June 2009, when three-point specialist Jason Kapono ended his two-year tenure with the Raptors, and was traded to the Philadelphia 76ers for the aggressive veteran forward Reggie Evans.^[2] Toronto then drafted DeMar DeRozan with the ninth pick, enabling them to fill a spot on the wings.^[3] The other major roster change came in the form of signing free agent Hedo Türkoğlu; this led to a sign-and-trade agreement involving four teams, with Toronto landing Devean George (who was later traded for Marco Belinelli) and Antoine Wright, while trading Marion, Kris Humphries and Nathan Jawai.^[4] Around the same time, Parker signed with the Cleveland Cavaliers, while Indiana point guard Jarrett Jack was signed to back up José Calderón and former Raptor Radoslav Nesterović was brought back to the fold. Finally, Carlos Delfino and Roko Ukić were moved to the Milwaukee Bucks for Amir Johnson and Sonny Weems.^[5] It became increasingly clear that Colangelo, in securing a credible nucleus for the future, was doing this to persuade Bosh to stay.^[6]

Regular season

The Raptors opened their season with a 101–91 home win over LeBron James' Cleveland Cavaliers.^[7] Bosh and Andrea Bargnani recorded impressive numbers—with Bosh leading the league in rebounds and free throw attempts, and also as one of the top scorers—but the Raptors were slow off the blocks, going 7–8 in their first 15 games. In that period, although the Raptors was fourth in the league in number of points scored per game, they were second last in the league in number of points allowed per game as well. Newcomer Wright criticised the team for being unfocused in pre-game preparations, and appealed to team captain Bosh to change that.^[8] The Raptors persisted in being one of the worst defensive teams in the league, and their descent culminated in a 146–115 drubbing by the Atlanta Hawks—the second worst defeat in franchise history—bringing their record to 7–13.^[9] They were soon ranked last in most points allowed per 100 possessions, earning a defensive rating that was 10.8% worse than the second-last team, which was the largest disparity in NBA history.^[10] The team held a meeting to clear up communication issues among teammates, and this was followed by three consecutive wins.^[11]

Türkoğlu was having difficulty adapting to his new team, while injuries were also an issue for the Raptors: Evans had yet to feature with more than a third of the season gone, while Calderón missed a dozen after 20 games into the season. This, however, allowed front court role players like Johnson and Weems to pick up more minutes, and Jack to start at the point. Toronto compiled a 5-game winning streak—its best in years—to climb back into the playoff race, and found themselves 16–17 to round off the year after a bad start to December, and .500 after 36 games. They were able to maintain this record for the next few games, beating premier teams such as the San Antonio Spurs, Orlando Magic, Dallas Mavericks and Los Angeles Lakers along the way, while Bosh continued leading the league in double doubles and was only one of three players to average at least 20 points and 10 rebounds a game. By the time the All-Star break arrived, the team had a 29–23 record, going 18–6 after the emergency team meeting in mid-December, which was the second best in the league after Cleveland.

After hitting a season-high of six games above .500, Toronto's run of good form came to a halt after the All-Star break, due in large part to an injury to Bosh which occurred in a Feb. 17 OT loss to Memphis.^[12] The team struggled and went under .500 on 14 March 2010, going 32–33. Their form in March continued to be patchy, and their drop in the conference rankings resulted in a close jostle with the Chicago Bulls for the eighth and final playoffs spot. Triano also adjusted the starting lineup, moving Türkoğlu and DeRozan to the bench and Wright and Weems in the opposite direction. As the Bulls closed in on the Raptors, Bosh and Türkoğlu suffered injuries, with the former being ruled out of the regular season five games before it ended.^[13] When Chicago subsequently routed Toronto, the eighth spot remained up for grabs until the final day of the regular season: if Toronto beat New York and Chicago lost to Charlotte, Toronto would prevail as they led the head-to-head 2–1; however, while the Raptors defeated the Knicks, the Bulls won against the Bobcats and Chicago took the final spot, with a record of 41–41, one win above Toronto.

Record vs. opponents

Regular season

Regular season

Trades

Free agents