Toronto Argonauts, with 16 wins between 1914 and 2012, both inclusive.
Winnipeg Blue Bombers, who have played in 24, winning 10.
Toronto Argonauts, with 16.
Toronto Argos with 16.
The Edmonton Eskimos beat the Ottawa Rough Riders on a last-second field goal. Edmonton was down 19 points at the half, but came back to win in one of the most exciting Grey Cup games.
All the teams which have won the Grey Cup, with only one exception, have been Canadian teams, which is to say that they were based in Canadian cities, including the most recent team to win it.
As of 2012, Calgary Stampeders who they defeated in the 100th Grey Cup.
The Grey Cup record which will likely never be broken is the record for the greatest margin of victory: 54 points by Queen's University over Regina in 1923. It is also the record for the most points scored by one team in a Grey Cup game, although that one might be broken someday (fifty points have twice been scored by one team in the Grey Cup).
Brazil have won the most games.
The Ottawa Rough Riders defeated the Edmonton Eskimos to win the 1960 Grey Cup.
Toronto Argonauts won their 16th Grey Cup in 2012.
1
Never. The Oilers are a hockey team and the Grey Cup is the championship trophy for professional Canadian Football.