Six: 1949, 1970, 1974, 1977, 2009, 2010.
6
Type your answer here... the riders won 6 cups
Three: 2002, 2009 and 2010
Winnipeg Blue Bombers have never even played in a Grey Cup in Winnipeg, never mind having won there.
Anthony Calvillo played for the Montreal Alouettes from 1998 until 2003. During that time, the Alouettes won three Grey Cups, in 2002, 2008, and 2009.
BC Lions have won the Grey Cup six times, most recently in 2011.
Seven: 1949, 1970, 1974, 1977, 2002, 2009, 2010.
Yes, after Toronto.
Montréal Alouettes have won seven, most recently in 2010. But Montréal AAA won in 1931 and the 1944 Grey Cup winners were the Ste Hyacinthe-Donnacona Navy Combines, a team made up of sailors who were stationed at naval bases in and near Montréal. That makes a total of nine Montréal Grey Cups.
The Hamilton Tiger-Cats, a team formed from the merger of two teams called the Tigers and the Wildcats, won their first Grey Cup of 8 in 1953. However the Tigers had won 5 before then and the Wildcats, an air force team, won one. A team from Hamilton called the Alerts also won one, making a total of 15 cups won by Hamilton teams. But the Ti-Cats have only won 8.
21 CUPS
Montréal won two Grey Cups in a row in 2009-2010. They appeared in three Grey Cups in a row in 1954-56, 1977-79 and again in 2008-2010 and played in successive Grey Cup games in 1974-5, 2002-3 and 2005-6. Of the nine years between 2002 and 2010, Montréal only missed playing in the Grey Cup twice.