What team has won the fewest Grey Cup Games?

Answer 1

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.