The Edmonton Eskimos? Nope. The Eskies have 13 Grey Cup victories, all since 1954, but the Toronto Argonauts have 16 wins, going back to 1914.
Ten of the Argo wins came between 1914 and 1952, including a threepeat in '45, '46 & '47.
The Green and Gold do, however, have the most Grey Cup appearances, with 22. And I'm not counting the 2 losses in 1921 and 1922, because it was not the same team, just a team with the same name.
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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.
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.
All of the present teams in the Canadian Football League (CFL) have their names engraved on the Grey Cup. Two former CFL teams were also Grey Cup winners: Ottawa Rough Riders and Baltimore Stallions. Several other non-CFL teams have won the Grey Cup, but none since 1944.
Toronto Argonauts-16 Grey Cups
1914, 1921, 1933, 1937, 1938, 1945, 1946, 1947, 1950, 1952, 1983, 1991, 1996, 1997, 2004, 2012.