The 104th Grey Cup (branded as the 104th Grey Cup presented by Shaw for sponsorship reasons) was a Canadian football game that was played on November 27, 2016, between the Calgary Stampeders and the Ottawa Redblacks, which decided the champion for the 2016 CFL season. In an upset, Ottawa defeated the heavily favored Stampeders 39–33 in overtime to win a championship in just their third season of existence. This was the third Grey Cup game to go into overtime (the other two instances came in 1961 and 2005). This also marked a first that a CFL team won its division with a losing record (8-9-1) and became the 3rd worst team (behind the 2000 BC Lions and 2001 Calgary Stampeders who both went 8-10) to win the Grey Cup.

The Redblacks ended a 40-year championship drought for the city of Ottawa that spanned three CFL franchises and 27 football seasons of play. The Redblacks became the fourth-fastest expansion team to win a championship in an established North American professional sports league, after the 1950 Cleveland Browns (who won a championship in their first season in the National Football League), the 1927–28 New York Rangers (who won the Stanley Cup in their second National Hockey League season) and the 1995 Baltimore Stallions (who, as part of the CFL’s mid-1990’s U.S. expansion, won the Grey Cup in their second and final CFL season); they are tied with the 1970-71 Milwaukee Bucks (winners of the National Basketball Association title in their third season).

The game was played at BMO Field in Toronto, Ontario.