Toronto Argonauts have 16. No other team has 15 or more.
The Hamilton Ticats are a Regular Cfl team that have won the Grey Cup 15 Time's
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.
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.
Montreals canadians
Montreal, 15
3/9=.33....Jay's team5/15=.33...Sam's team
Nineteen: won 4 lost 15.
The Pittsburgh Steelers had the most regular season wins with 15. Including playoff wins, the New England Patriots had the most with 17.
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.
The Oakland A's In 2012 With 15 Walk Off wins in a single season.
The Hamilton Tiger-Cats, a team formed from the merger of two teams called the Tigers and the Wildcats, won their first Grey Cup of 8 in 1953. However the Tigers had won 5 before then and the Wildcats, an air force team, won one. A team from Hamilton called the Alerts also won one, making a total of 15 cups won by Hamilton teams. But the Ti-Cats have only won 8.
Toronto, having hosted it 47 times. No other city comes close: Vancouver is nearest at 15.