What are the odds that we have one of the best (picked to bring the Stanley Cup back to it's birthplace) teams in the NHL, and at the same time have possibly the worst (officially if we get beat by the lowly Ti-cats even once of the two remaing encounters) team in the CFL in the same year?
We're not called "Hockey Country" for nothing! 
The odds aren't all that bad. Following the Flames Stanley Cup run (which should have ended with a win in game 6 against Tampa Bay), Calgary fielded the crappiest team of the CFL, winning only four games.
So it is very possible that you guys shoot for the moon in hockey.
Though I don't know what are the odds that such a thing happen twice in a timelaps this short.