The 2 most prominent meetings between these clubs happened in 1986 and 1989, both of which were Stanley Cup Finals. The Habs won the '86 Championship, while the Flames were the very first team to hoist Lord Stanley in Montreal's Bell Center in '89.
Despite the -15 degree weather, McMahon Stadium was filled from end to end in jerseys of red, with a surprising amount of blue and white as well. At least the sun was shining and the beer and hot chocolate flowed freely.
Opening ceremonies included a quick aerial show of 5 jets above the stadium, performances by Tokyo Police Club, Paul Brandt singing the national anthem, and the ceremonial puck drop that saw legends Bob Gainey and Lanny McDonald on the ice with Jarome Iginla and Brian Gionta.
It was an exciting game, with both teams playing well but there were 2 key factors that determined the outcome.
1. Calgary's offence was just too much for Carey Price. Rene Borque's two goals and Anton Babchuk's slick move boosted the Flames to a 4 goal lead over the Habs.
2. Kiprusoff was a door. Despite windy conditions going against him, Kipper denied any chance of a Habs goal and earned his 41st career shutout.
In NHL outdoor game history, the visiting team was usually the one to skate away with a victory, but the Flames, who have been very hot of late, picked up the two points this time around. A home win over a storied rival helped add to the electric "C of Red" atmosphere.
It had been 8 years since the last outdoor NHL game was played in Canada, but it seemed to be well worth the wait. Overall, the Heritage Classic weekend was a success, and it became clear early on that hockey fans are unlike any other; willing to sit for hours in weather well below freezing, all for the love of the game.

Calgary Flames vs Montreal Canadiens, February 20th, 2011



Both teams were held scoreless throughout regulation, and in the first minutes of OT Ryan O' Reilly scored the only goal of the game for Colorado. But the real story of the night was the specatcular 51 saves made by Craig Anderson. Needless to say, Anderson received a standing ovation that night. 
PJ Stock and Stephen Peat get involved in a brawl deemed hockey's best fight ever, with each player landing over 20 hard shots on the other. After the fight was broken up, Stock skated away while giving his signature post-brawl wave to the hysterical crowd.
After scoring one goal and assisting another, Sidney Crosby topped off the night by lending a hand to Marc-Andre Fleury, stopping a goal from going into the Penguins' net while the Fleury was otherwise occupeid.