Toronto's brutal stretch of five games in seven days began with a resounding 113-90 loss at home to the Orlando Magic on Sunday.
Dwight Howard had 29 points and 14 rebounds to lead Orlando (36-10). The Magic made 13 of 40 attempts from beyond the three-point line.
Mickael Pietrus came off the bench for 22 points, with Jameer Nelson good for 18 to go along with nine rebounds and seven assists.
Jose Calderon was top scorer for Toronto with 16 points. Joey Graham had 14 points and 12 rebounds.
"It's frustrating obviously, it just wasn't a good day for us any way you look at it," said Toronto's Anthony Parker. "We didn't shoot the ball well, we didn't seem like we executed well offensively. Even when we got shots that we worked the offence to get, they just didn't fall in."
The Raptors were competitive in the first half, but not a factor after a Magic run early in the third.
Toronto (19-30) heads to Cleveland's building on Tuesday, where the Cavaliers are 22-0, and host Western leaders the Los Angeles Lakers on Wednesday.
The week concludes with games Friday in New Orleans and the following night in Memphis.
Chris Bosh had one of his tougher outings of the season, with 11 points and nine rebounds.
"I just didn't make shots," said Bosh, who struggled by going 4-for-11 from the field. "Dwight played very far off me a couple of times, usually I have the patience to knock those shots down but for some reason I was really in a hurry. I shouldn't have been like that."
The capacity crowd of 19,800 booed after a couple of Bosh's missed shots.
"I don't think the energy is good. The energy in the building isn't good," Bosh said afterward. "We get down a little bit and everybody is like 'Oh my god.' Everything just goes to shambles and I think we feed off that too much. We can't pay attention to what's in the stands.
"I don't boo," he added. "If you have a bad fiscal year, how about I boo you?"
Nelson had the hot hand early, pouring in 10 points in the first to give Orlando a 31-25 lead after one quarter.
Graham made a pair of free throws and a layup as Toronto pulled even at 33 in the second and the Raptors briefly led after Will Solomon's three-pointer.
But Howard came to life with key rebounds as well as points as Orlando restored its lead.
Toronto's Andrea Bargnani dunked to make it 51-47 Orlando, and after a pair of Nelson free throws, both teams were cold in the first half's final moments.
The Raptors continued shooting blanks to begin the third, but the Magic gradually found their legs, amassing a 19-point lead.
In addition to continued contributions from Howard and Nelson, Rashard Lewis hit a key three-pointer.
Orlando led 87-65 after three quarters and along with several points from Pietrus, Hedo Turkoglu hit a three to keep the margin wide for the Magic.
Toronto is just 9-14 at home, but one of the victories was a 104-102 nod over Orlando on Jan. 9.
It was one of the Raptors' gutsiest efforts this NBA season, with Calderon and Jermaine O'Neal on the sidelines.
Orlando has an NBA-best 18 wins on the road.