One of these years no doubt.
The Calgary Stampeders played their first game on Oct. 27, 1945 in Regina against the Roughriders - a 3-1 win. There was no regular season in 1945 and this was the first game of a two-game total-point playoff series. The Stamps won the series 15-1 before losing to Winnipeg in the West final. Calgary's first game at Mewata Stadium (Calgary) was an exhibition tilt on Oct. 20, 1945.
On November 27, 1994, the Baltimore Stallions narrowly lost the 82nd Grey Cup Game, played at Vancouver's B.C. Place, to the British Columbia Lions, by a score of 26-23. A year later, on November 19, 1995, the Stallions won the 83rd Grey Cup Game at Taylor Field in Regina, decisively defeating the Calgary Stampeders 37-20. The Baltimore franchise was later moved to Montreal and became the latest incarnation of the Alouettes.
Montreal Canadiens
The Calgary Flames won the Stanley cup in 1989. They did not make the playoffs in the 2013 season.
Calgary Flames
The Montreal Canadiens in 1989.
One, in Calgary (89)
The grey cup.
They defeated the Montreal Canadiens.
While the Atlanta Flames were relatively successful on the ice, they never won a Stanley Cup. However, the Flames were sold to new owners, moved to Calgary and did win a Cup as the Calgary Flames in the 1988-89 season.
1989
This depends on the sport/team. See related questions or re-ask your question.