<P> The Edmonton Eskimos have made the most appearances ( 25 ) , while the Toronto Argonauts have won the most championships ( 17 ) and have the best record in the Grey Cup composite standings ( 17 - 6 ) . Despite the CFL 's short - lived U.S. expansion in the mid-90's , the Grey Cup was never played outside of Canada . The Baltimore Stallions were the only American team to appear in the Grey Cup ( twice , losing in 1994 and winning the following year ) . Although the first Grey Cup game was in 1909 , none were played from 1916 to 1919 , so the 2012 Grey Cup was the 100th . The 104th Grey Cup was played on November 27 , 2016 at BMO Field in Toronto , with the Ottawa Redblacks defeating the Calgary Stampeders 39 -- 33 in overtime to win their first championship as a franchise and the first for the city of Ottawa since the defunct Ottawa Rough Riders won in 1976 . </P>
<P> The Edmonton Eskimos have made the most appearances ( 25 ) , while the Toronto Argonauts have won the most championships ( 17 ) and have the best record in the Grey Cup composite standings ( 17 - 6 ) . Despite the CFL 's short - lived U.S. expansion in the mid-90's , the Grey Cup was never played outside of Canada . The Baltimore Stallions were the only American team to appear in the Grey Cup ( twice , losing in 1994 and winning the following year ) . Although the first Grey Cup game was in 1909 , none were played from 1916 to 1919 , so the 2012 Grey Cup was the 100th . The 104th Grey Cup was played on November 27 , 2016 at BMO Field in Toronto , with the Ottawa Redblacks defeating the Calgary Stampeders 39 -- 33 in overtime to win their first championship as a franchise and the first for the city of Ottawa since the defunct Ottawa Rough Riders won in 1976 . </P>
who has won the most cfl grey cups
who has won the most cfl grey cups
the Toronto Argonauts
the Toronto Argonauts