Who has the most CFL Grey Cup wins of all time?

Answer 1

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.

Answer 2

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).

Answer 3

The Toronto Argonauts have won the most Grey Cup championships (16), followed by the Edmonton Eskimos (14) and Winnipeg Blue Bombers (10). The Winnipeg Blue Bombers have made the most Grey Cup appearances (24).

Answer 4

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.

Answer 5

3 players are tied for this record. Jack Wedley, Bill Stevenson and Hank Ilesic have each won 7 grey cups.

Answer 6

Warren Moon