As of 2012, Toronto Argonauts have appeared in 22 Grey Cup Games. They rank third in appearances, behind Winnipeg Blue Bombers (24) and Edmonton Eskimos (22), but are clearly first in victories with 16, against only 6 defeats.
Toronto has 16 Grey cups in 22 appearances. However, the question asked about "CFL" Grey Cup wins. The CFL was founded in 1958. Therefore, Grey Cup wins prior to 1958 don't count. Only Grey Cup wins since 1958 count in answering the question properly, and Edmonton Eskimos have won the Grey Cup ten times since then, more than Winnipeg's seven. Toronto, Montreal, Hamilton and BC have had six, Calgary five and Saskatchewan four (as of 2012).
Regardless of what union or organization was in control of the Grey Cup, there has been a total of 20 teams to win in 101 years of competition (as of 2013) :
Toronto Argonauts 16
Edmonton Eskimos 13
Winnipeg Blue Bombers 10
Ottawa Rough Riders 9
Hamilton Tiger-Cats 8
Montreal Alouettes 7
BC Lions 6
Calgary Stampeders 6
Hamilton Tigers 5
Saskatchewan Roughriders 4
University of Toronto Varsity Blues 4
QueensUniversity 3
Sarnia Imperials 2
Toronto Balmy Beach 2
Baltimore Stallions 1
Hamilton Alerts 1
Hamilton Flying Wild Cats 1
Montreal AAA Winged Wheelers 1
Montreal HMCS Donnacona 1
Toronto RCAF Hurricanes 1
The same argument can be made of the Stanley Cup. It was first awarded in 1893, yet the NHL didn't assume full control until 1927. This fact doesn't belittle the victories of the Victoria Cougars (1925), the Vancouver Millionaires (1915), the Kenora Thistles (1907) or the Quebec Bulldogs (1912, 1913), to name a few.
The Montreal Amateur Athletic Association is the only group to win both the Stanley Cup (1893) and the Grey Cup (1931). Of note, Queen's University has won the Grey Cup (1922, 1923, 1924) and lost the Stanley Cup (1895, 1899, 1906).
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.
Toronto Argos with 16.
As of 2013, all eight CFL teams have at least one Grey Cup victory to their credit. As of 2014 there are nine teams: the new Ottawa Redblacks have no Grey Cup wins unless you count the wins by the Ottawa Rough Riders.
Montreal, 15
The Hamilton Ticats are a Regular Cfl team that have won the Grey Cup 15 Time's
Montreal canadians have won the Stanley |Cup 24 times, the most in history and seriously...who cares about the cfl
Winnipeg Blue Bombers, who have played in 24, winning 10.
Of current CFL teams, Saskatchewan Roughriders have 4 Wins - 1966,1989,2007, and 2013 The above is only the answer to the question if one restricts the question to current CFL teams. The CFL teams that were in the USA, with the exception of Baltimore, collectively had zero Grey Cup wins. But the question was wide open. The correct answer would be that dozens of teams have no Grey Cup wins. One must remember that the Ontario Rugby Football Union (ORFU) regularly challenged for the Grey Cup right up until the mid-1950s. Only three ORFU teams ever won the Grey Cup. The Sarnia Imperials and Toronto Balmy Beach each had two victories, and the Hamilton Wildcats one. But there were several teams in the ORFU from time to time, none of which ever won (or even played in) a Grey Cup game. There were also a number of eligible teams out west that never made it to the big game. Likewise, going back to the days when the university teams could challenge, only University of Toronto (4 wins) and Queens University (3 wins) ever played in a Grey Cup game. The rest never got on the field. The true number of teams that were eligible to challenge but never made it, and therefore won zero Grey Cup games, might never be known. And, of course, teams which never played Canadian Football have never won it either.
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.
The CFL season begins in June and ends with the Grey Cup game, played in late November or early December.
Winnipeg Blue Bombers with 10 (last in 1990) after Toronto Argonauts' 16 and Edmonton Eskimos' 13.
The Stanley Cup is the oldest professional sports trophy in North America. It was donated by the former Governor General of Canada Lord Stanley of Preston in 1892 as an award for Canada's top-ranking amateur ice hockey club. Today, it is the top trophy of the National Hockey League (NHL).
27 wins: MLB - New York Yankees (40 total appearances)24 wins: NHL - Montreal Canadiens (34 total appearances)17 wins: NBA - Boston Celtics (20 total appearances)15 wins: CFL - Toronto Argonauts (21 total appearances)15 wins: NBA - Los Angeles/Minneapolis Lakers (28 total appearances)13 wins: CFL - Edmonton Eskimos (22 total appearances)13 wins: NHL - Toronto Maple Leafs (21 total appearances)11 wins: NHL - Detroit Red Wings (23 total appearances)10 wins: CFL - Winnipeg Blue Bombers (23 total appearances)10 wins: MLB - St. Louis Cardinals (17 total appearances)9 wins: MLB - Oakland/Philadelphia Athletics (14 total appearances)9 wins: NFL - Green Bay Packers (12 total appearances)8 wins: CFL - Hamilton Tiger-Cats (18 total appearances)8 wins: CFL - Ottawa Rough Riders (14 total appearances)7 wins: MLB - Boston Red Sox (11 total appearances)8 wins: NFL - Chicago Bears** (10 total appearances)6 wins: CFL - Calgary Stampeders (12 total appearances)6 wins: NFL - New York Giants (12 total appearances)6 wins: NFL - Pittsburgh Steelers (7 total appearances)6 wins: MLB - Los Angeles/Brooklyn Dodgers (18 total appearances)6 wins: NBA - Chicago Bulls (6 total appearances)5 wins: NHL - Boston Bruins (17 total appearances)5 wins: MLB - San Francisco/New York Giants (17 total appearances)5 wins: CFL - Montreal Alouettes (16 total appearances)5 wins: MLB - New York Giants (14 total appearances)5 wins: CFL - Calgary Stampeders (11 total appearances)5 wins: NFL - Washington Redskins (11 total appearances)5 wins: CFL - B.C. Lions (9 total appearances)5 wins: MLB - Cincinnati Reds (9 total appearances)5 wins: NFL - Dallas Cowboys (8 total appearances)5 wins: CFL - Hamilton Tigers (8 total appearances)5 wins: MLB - Philadelphia Athletics (8 total appearances)5 wins: MLB - Pittsburgh Pirates (7 total appearances)5 wins: NHL - Edmonton Oilers (7 total appearances)5 wins: NBA - Minneapolis Lakers (6 total appearances)5 wins: NFL - San Francisco 49ers (5 total appearances)