As of 2012, the Toronto Argonauts have won 16 Grey Cup games, but only 6 of those have occurred since 1952.
Other Toronto-based teams have won a further 7, but all those occurred before the end of World War II.
The Toronto Argonauts have the most Grey Cup victories: 16.
Winnipeg Blue Bombers have never even played in a Grey Cup in Winnipeg, never mind having won there.
Winnipeg Blue Bombers, who have played in 24, winning 10.
It's been played in Winnipeg three times, first in 1991.
The Winnipeg Blue Bombers are a team in the Canadian Football League. They are located in Winnipeg, Manitoba. They were the first team from Western Canada to win the Grey Cup.
BC defeated Montreal 25-14 in a game played in Winnipeg.
Winnipeg has won the Stanley Cup 3 times. 1896 Winnipeg Victorias 1901 Winnipeg Victorias 1902 Winnipeg Victorias Neither the current incarnation of the Winnipeg Jets nor the previous one has won a Stanley Cup.
BC Lions have won the Grey Cup six times, most recently in 2011.
The CFL was formed in 1958. Since then Hamilton has lost 11 times, Edmonton and Montréal 8, Saskatchewan 7, Winnipeg and Calgary 6, BC 4, and Toronto 3. If you include Grey Cup losses before 1958, Saskatchewan lost a further 8 games (total 15), Winnipeg also a further 8 (total 14), Toronto 3 (total 6), Montréal 3 (total 11), Calgary 1 (total 7), and Edmonton 1 (total 9). If you include two losses by Winnipeg RCAF teams that makes 16 for them. Hamilton Tiger Cats did not lose any Grey Cup games before 1958, but Ticat fans like to count the Grey Cup victories of their predecessor teams the Tigers and the Wildcats, so to be fair one ought to count the three losses by the Tigers and the one by the Wildcats, giving Hamilton a total of 15 like Saskatchewan.
If the question is, "How many times did the same two teams appear in the Grey Cup two years in a row?" the answer is, lots. In some cases the same teams were in the Grey Cup for three years running, which I would count as two rematches, that is, two games where the teams were the same teams as the year before. So, how many times has the Grey Cup been between the same two teams who were in it the year before? Over 101 Grey Cup games, 16 times, most recently in 2009-2010.
The game in 2012 was the 100th Grey Cup game.
They never won a Stanley Cup. They won 6 times during the challenge cup era, but they were called the Winnipeg Victorians.
It depends on how you define a team. The Saskatchewan Roughriders, formerly Regina Roughriders, have lost 15 Grey Cup Games. The Hamilton Tiger-Cats and their predecessor teams the Tigers and Wildcats (whose victories are always counted with Hamilton's) have also lost a total of 15. Winnipeg Blue Bombers have lost the game 14 times, but if you count the two losses by the Winnipeg RCAF team during the war, that makes 16.