Toronto Argonauts have won the Grey Cup 16 times, most recently in 2012.
Edmonton Eskimos with 13, after Toronto Argonauts with 16.
If the question is, "How many times did the same two teams appear in the Grey Cup two years in a row?" the answer is, lots. In some cases the same teams were in the Grey Cup for three years running, which I would count as two rematches, that is, two games where the teams were the same teams as the year before. So, how many times has the Grey Cup been between the same two teams who were in it the year before? Over 101 Grey Cup games, 16 times, most recently in 2009-2010.
The two Argonauts were the son of the North wind.
Boreas, who fathered the Argonauts Zetes and Calais.
The Ottawa Rough Riders won their first Grey Cup in 1940, defeating Toronto Balmy Beach, in the only two-game 'total points' Grey Cup Championship.
O.J. Brigance won a Grey Cup with the Baltimore Stallions in 1995 and a Super Bowl with the Baltimore Ravens in 2000 (Super Bowl XXXIV). Tyrone Williams won a Grey Cup with the Toronto Argonauts in 1996 and a Super Bowl with the Dallas Cowboys, although he did not play in the game (Super Bowl XXVIII). Harald Hasslebech won a Grey Cup with the Calgary Stampeders in 1992 and two Super Bowls with the Denver Broncos (Super Bowls XXXII and XXXIII). Barry Wilburn is listed as having won with the BC Lions and Washington Redskins. Terry Greer also had a Grey with Toronto and a SB with 9ers
Actually, there are currently three Lionel Conacher, Gerry James and Wayne Gretzky. Both Gerry James and his father Eddie "Dynamite" James have their names engraved on the Grey Cup. They have both been inducted into the Canadian Football Hall of Fame as well. Eddie James was the roughest, toughest player in the west, and was a member of the Winnipeg Pegs, the first western Canada team to win the Grey Cup (1935). Gerry James played in a Grey Cup final and the Stanley Cup final in the same season. He once played in a Grey Cup game one Saturday afternoon as a Winnipeg Blue Bomber and in an NHL game as a Toronto Maple Leaf the same evening. Wayne Gretzky was a minority owner of the 1991 Toronto Argonauts. Orginally the CFL only included majority owner Bruce McNall in the engraving. The CFL added the two minority oners (the other being John Candy) in 2007.
North Wind, Boreas.
Uruguay has won the world cup two times.
France have won the Europen cup on two times .
All of the present teams in the Canadian Football League (CFL) have their names engraved on the Grey Cup. Two former CFL teams were also Grey Cup winners: Ottawa Rough Riders and Baltimore Stallions. Several other non-CFL teams have won the Grey Cup, but none since 1944.