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.
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Toronto has won a total of 21 Grey Cup Games: Toronto Argonauts (15); Toronto Varsity Blues (4); Toronto Balmy Brach (2).
15, the most in the CFL
Toronto Argonauts have won 16 Grey Cups, the last of which was in 2012. However, only 6 of these were won after the creation of the CFL in 1958.
The Winnipeg Blue bombers have won 10 Grey Cups, the 1st one was in 1935, and the last one was in 1990.
The Toronto Argonauts won their 1st Grey Cup in 1914; they won their last one in 2004.