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.
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Hamilton Ti-Cats have won 8 Grey Cups. However other teams from Hamilton have also won including Hamilton Alerts, Hamilton Flying Wildcats, and the Hamilton Tigers who won five times, a total of 7. So teams from Hamilton have won 15 Grey Cups.