The city has a reputation during recent NHL playoff runs for its spontaneous celebrations that occasionally deteriorate into rampages of vandalism, looting and violence.
In the only Canadian city hosting playoff hockey this year and with the team's biggest rivals in town, authorities say they're ready for anything, with the series tied 1-1 heading back to Montreal.
Anie Samson, the city council member in charge of public security, said the administration is prepared ahead of Tuesday's Game 3 at the Bell Centre.
"We are concerned about (potential problems), but we are working with the police and we have a plan," said Samson. "We are ready and we hope it's going to work."
The downtown core is always at the center of the celebration and more, and memories of smashed windows are still fresh for some downtown business owners. An association that represents them says there is always some trepidation.
"There's a certain level of worry because we've felt the negative effects during the playoffs," said Andre Poulin, who heads Destination Centre Ville. "But at the same time, we're confident the police will deploy necessary resources to protect our businesses."
Montreal's history of Stanley Cup riots is well documented, with the Canadiens' most recent Stanley Cup triumphs in 1986 and 1993 marred by hooliganism. In recent years, an early-round victory has been enough to set off rioting.
The worst came in April 2008 after the Canadiens' seventh-game playoff win against the Bruins. It culminated with police cars being burned and downtown businesses being looted.
At least 16 people were arrested and damage to police property was evaluated at $500,000.
It happened again in May 2010, with windows smashed amid clashes between rioters and police on Ste-Catherine Street following a defeat of the Pittsburgh Penguins in the second round.