Toronto Argonauts have 16 Grey Cup wins from their first in the 6th Grey Cup in 1914 to their win in the 100th Grey Cup in 2012. The team that has won the most grey cups in a row would be the Edmonton Eskimos who won 5 in a row between 1978-1982.
Hank Ilesic and Bill Stevenson are tied with seven CFL Grey Cup victories. Jack Wedley also was on the Grey Cup winning team seven times, but that was in the days before the CFL. My father was on six Grey Cup winners and one losing side. Again, that was before the CFL. Seven different players are tied for most Grey Cup appearances, with nine.
Winnipeg (21)
Edmonton Eskimos with 13
Toronto Argos with 16.
Toronto has won a total of 23 grey cups but that isn't the answer to the question. First, the question asked which team, not which city. Second, the question specified winning Grey Cups in the Canadian Football League. The CFL was not formed until 1958, so Grey Cup victories prior to 1958 don't count. The correct answer is the Edmonton Eskimos, with ten Grey Cup victories (and eight losses, which also qualifies the Eskies for most appearances). Grey Cup victories for Toronto teams include 4 by U of T, 2 by Balmy Beach, 1 by Toronto RCAF, and 16 by Argonauts.
Hamilton and Toronto are tied with the most with 15 each
Winnipeg Blue Bombers, who have played in 24, winning 10.
The Canadian Football League (CFL) did not come into being until 1958, therefore Grey Cup Games played prior to 1958 do not count. As of the end of 2008, Edmonton has the most appearances with 18, followed by Hamilton with 16.
Yes. In the 1990s the governors of the CFL thought they could expand the league into the United States. A number of new teams were created, most of which quickly folded. Only the Baltimore team did well, winning the Grey Cup in 1995. However, the next year the Baltimore team was moved to Montreal and that was the end of American teams in the CFL.
The Hamilton Ticats are a Regular Cfl team that have won the Grey Cup 15 Time's
Winnipeg Blue Bombers with 10 (last in 1990) after Toronto Argonauts' 16 and Edmonton Eskimos' 13.
The Canadian Football League (CFL) was founded in 1958. The Grey Cup has been in the exclusive possession of the CFL since then. The Grey Cup Game has been played annually in the CFL since 1958. Currently there have been 97 Grey Cup Games