Riot police in Vancouver used tear gas to quell violence that broke out after the Vancouver Canucks lost the final game of the Stanley Cup.
Cars were set on fire and shops were looted following the ice hockey team's 4-0 defeat to the Boston Bruins.
Mobs of angry fans roamed central Vancouver after the game, as thick acrid smoke rose over the city centre.
Similar riots broke out in the Canadian city after the Canucks lost the Stanley Cup in 1994.
Record crowds of supporters gathered in the heart of the city on Wednesday in the hope of seeing their team - the favourites - secure the Stanley Cup and be crowned winners of the National Hockey League (NHL).
But hope quickly turned to gloom after the Boston Bruins scored first and then went on to secure an emphatic victory.
As soon as the final buzzer sounded, a hail of beer bottles rained down on the giant outdoor television screens, the Associated Press reports.
People chanted obscenities, and witnesses said some people took out their anger on nearby cars, flipping two over and setting them alight.
Shops were also reported to have had their windows smashed and then looted.
Some fans were seen trying to hold back more unruly members of the crowd, without much success.
A line of 10 riot police tried to hold back a crowd of several thousand in one part of central Vancouver, Canada's Globe and Mail newspaper reported.
Officers were pelted with bottles and firecrackers; streets were filled with rubbish, broken glass and streams of alcohol.
"It's so sad to see this happen again," Larissa VanDam told the Globe and Mail. "This is a real black eye on our city. We saw this happen in 1994 and I was so, so hoping it wouldn't happen again."
Vancouver mayor Gregor Robertson described the scenes as "embarrassing and shameful".
"The vast majority of people who were downtown were there to enjoy the game in a peaceful and respectful manner," he said.
"It is unfortunate that a small number of people intent on criminal activity have turned pockets of the downtown into areas involving destruction of property and confrontations with police."
The Canucks had the NHL's best regular-season record, but have never won the Stanley Cup since entering the league 40 years ago.