The Saskatchewan Roughriders have won the cup 4 times, most recently in 2013. However, you might have been thinking of the Ottawa Rough Riders (spelled differently as you see). They won the Grey Cup 9 times.
Nineteen: won 4 lost 15.
Four times, most recently in 2010.
1989
Eagle Keys
The Sarnia Imperials won their second Grey Cup in 1936, defeating Ottawa.
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.
BC Lions have won the Grey Cup six times, most recently in 2011.
Saskatchewan's opponents in 1989 were the Hamilton Tiger-Cats.
Who was the Backup Full Back for George Reed in the 1966 Grey Cup
For the Grey Cup they played against the Saskatchewan Roughriders, which they won.
The game in 2012 was the 100th Grey Cup game.
13 times