1. All 7 Canadian teams make the playoffs



2. The 3 Canadian teams from the Atlantic Division each play an American team in the 1st round and win.



3. The 3 Canadian teams from the Pacific Division each play an American team in the 1st round and win.



4. Winnipeg plays the #3 seed from the Central Division in the 1st round and wins.



5. By the start of the 2nd round, every Western Conference team still in the playoffs is Canadian.



6. By the start of the 2nd round, the last remaining American team in the playoffs, which will be from the Metro Division, is eliminated by a Canadian team.



7. When the Conference Finals get underway, a Canadian team is guaranteed to win the Cup because all 4 Canadian teams in the Conference Finals will be Canadian.

Good luck getting all 7 Canadian teams to make the playoffs in a single year lol, and I say that as a Canadian

Even if all 7 Canadian teams made the playoffs, they would be competing against 9 American teams for the Cup.

The 7 Canadian teams would also have to avoid playing each other.

Furthermore, an American team makes the playoffs for every Canadian team that misses the playoffs.

All in all, Canada's cup drought is not ending any time soon.