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.
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.
Edmonton Eskimos with 13
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
Hamilton and Toronto are tied with the most with 15 each
I might be wrong in this question but i know 2 people who have the most wins in The CFL. One Is Wally Buono And Don Matthews. As I said i might be wrong but these are the names that came to my head.
The Hamilton Ticats are a Regular Cfl team that have won the Grey Cup 15 Time's
The Grey Cup