Massa crashed twice at the Monaco Grand Prix two weeks ago: once during practice and another during the race that sent him to hospital.
The Brazilian, who was released after a precautionary medical examination, lost control of his car again Saturday during qualifying under drizzling rain that fell on Montreal's Circuit Gilles Villeneuve.
Massa's Formula One car spun sideways while breaking into the third turn, slid off the track across a patch of grass and slammed into a wall. The 32-year-old, ranked No. 7 in the standings, smacked his steering wheel a few times with his hands in frustration.
"When the rear end broke away, there was nothing I could do anymore," Massa said.
"Physically, I'm fine, but... I'm very disappointed. Never before have I had three accidents in such close succession."
The unpredictable weather was a major concern for drivers, including Ferrari teammate Fernando Alonso.
The Spaniard, who sits third in the overall drivers' rankings, said that lap after lap the track conditions and tire grip changed dramatically.
"It's very easy to get it wrong," Alonso said, before addressing Massa's wipeout.
"Obviously, we're a little bit disappointed because we felt very competitive this weekend with the car, and (now) we will start sixth and (16th)."
Ferrari, which is second in the constructors' standings, had reason for optimism a month ago when both Alonso and Massa stood on the podium following the Spanish Grand Prix. Alonso won the race and Massa finished third, placing them ahead of their Red Bull rivals, Formula One leader Sebastian Vettel and Mark Webber.
But Monaco proved to be a much bigger challenge, as Massa failed to complete the race after hitting a wall and Alonso finished seventh behind both Vettel and Webber.
Vettel won the pole position for Sunday's Canadian Grand Prix and Webber will start fifth.
Alonso remained optimistic since Kimi Raikkonen of Lotus, the driver between him and Vettel in the drivers' standings, will start from the 10th position.
"Obviously, if we can finish in front of our rivals in the championship it would be great. Kimi is starting in tenth — it's a good opportunity. Sebastian will be more difficult — we need a very good race," he said, adding he hoped for dry conditions.
"Starting from sixth here isn't bad, because you can overtake at this circuit."
For his part, Massa was pleased with his pace before the crash and he said he plans to be on the attack Sunday.
"On this track, anything can happen," Massa said.