Yes, in 2008
The Calgary Stampeders won the Grey cup in 2001.
Calgary Stampeders, they beat Montreal 21-14
On November 19, 1995, the Baltimore Stallions won the 83rd Grey Cup Game at Taylor Field in Regina, defeating the Calgary Stampeders by a score of 37-20.
Saskatchewan has never played Calgary in the Grey Cup. Because of the crossover playoff rule, it is now possible to have a "West vs. West" Grey Cup but it has never happened. Perhaps you are thinking of the Ottawa Rough Riders, who Calgary defeated to earn their first Grey Cup in 1948.
Toronto Argonauts won their 16th Grey Cup in 2012.
Calgary Stampeders
The Calgary Flames won the Stanley cup in 1989. They did not make the playoffs in the 2013 season.
Edmonton Eskimos have won the Grey Cup exactly 13 times. Toronto Argonauts have won the Grey Cup more than 13 times. They have 16.
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
Toronto Argonauts have won the Grey Cup 16 times, most recently in 2012.
Yes, the Calgary Flames won the Stanley Cup in 1989.
Saskatchewan