The only reason the Calgary Flames are not higher on this list is because they have video footage of their one-and-only championship, and the footage is in color (unlike for some other Canadian franchise on this list … ahem …). Since their Stanley Cup Final appearance in 2004 when they lost to the Lightning, the Flames have won just three playoff series and have never made it past the second round. Their arena is terrible, and the new one won’t be ready until at least the 2026-27 season. Following the Matthew Tkachuk trade to the Florida Panthers, where the Flames wound up with a Jonathan Huberdeau who can’t break the 60-point mark, it’s hard not to be pessimistic about a franchise in desperate need of a top-to-bottom rebuild. Not to mention, you never see sunny days when you’re living in the shadow of your provincial rival in the Oilers. But hey, at least they have the Stampede!