Has any gray Cup hosting team actually won the gray Cup?

Answer 1

The Grey Cup Game is not hosted by a team, it is hosted by a city. Until 1954, the Grey Cup Game was almost always played in Toronto, because the largest stadium in Canada at the time (Varsity Stadium) was located in Toronto.

From the time the Grey Cup was donated by the Governor General (1909) until 1952, Toronto-based teams had won the Grey Cup Game (played in Toronto) 17 times.

Since the Canadian Football League (CFL) was established in 1958, the Grey Cup has been the exclusive property of the CFL. The following CFL teams have played in a Grey Cup Game held in the team's city:

1963 B.C. Lions (Vancouver) (loss)

1972 Hamilton Tiger-Cats (win)

1977 Montreal Alouettes (win)

1979 Montreal Alouettes (loss)

1982 Toronto Argonauts (loss)

1983 B.C. Lions (Vancouver) (loss)

1994 B.C. Lions (Vancouver) (win)

2002 Edmonton Eskimos (loss)

2012 Toronto Argonauts (win)

As you can see, playing on home ground does not seem to improve nor hurt the chances of winning the Grey Cup.