Toronto Argonauts have won 16 Grey Cups, the last of which was in 2012. However, only 6 of these were won after the creation of the CFL in 1958.
Australia have won three consecutive world cups
Three: 2002, 2009 and 2010
The Winnipeg Blue bombers have won 10 Grey Cups, the 1st one was in 1935, and the last one was in 1990.
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.
B.C has won 6 Grey Cups, the first in 1964, then 1983, 1994, 2000, 2006 and 2011.
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.
3 players are tied for this record. Jack Wedley, Bill Stevenson and Hank Ilesic have each won 7 grey cups.