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.
Well, the team will have to win 4 games in a row out of the 7 games.What games are counted, and by which teams?Only Stanley Cup Finals gamesOnly games by the Stanley Cup Champion in the Stanley CupGames by the Stanley Cup Champion including regular season games
Hamilton and Toronto are tied with the most with 15 each
boston bruins
The Stanley Cup final format is a best 4 out of 7. The team that wins 4 games first is the winner. The fewest number of games that could be played is 4 and the highest number of games that could be played is 7.
Winnipeg Blue Bombers, who have played in 24, winning 10.
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.
As of 2012, Calgary Stampeders who they defeated in the 100th Grey Cup.
The Stanley Cup was donated in 1893, making it the oldest trophy in professional team sports. The Grey cup was donated in 1909.
Toronto Argonauts, with 16 wins between 1914 and 2012, both inclusive.
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
The Ottawa Rough Riders defeated the Edmonton Eskimos to win the 1960 Grey Cup.
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.