1992-93 During the 100th anniversary of the Stanley Cup, it would have been fitting to see the Habs vs the Leafs in the Cup final. I wanted to see it so badly that year, but didn't happen. Now the way things are going for both teams, I'm not sure whether it will ever happen in my lifetime.
That's the series I thought of when I saw that thread, and it was soooo close to happening - but then LA had to win game 7. Now that the Leafs & Habs are in the same conference, you'll never see them play in the Stanley Cup Final under the currernt system. If both teams can get it together, you could see a Toronto-Montreal series in one of the first three rounds.
1993 (was Mon/LA) - Montreal vs Toronto
2002 (was Det/Car) - Detroit vs Toronto
* I'll also add that if Montreal beat Carolina in the 2nd round, it would have been a Montreal-Toronto Eastern Conferance Final
2003 (was NJ/Ana) - Ottawa vs Vancouver
Ottawa lost to New Jersey in the ECF while Vancouver lost to Minnesota in the 2nd round. Both teams were good in the regualar season, the Western Conference was in transition as the big 3 (Detroit, Colorado, and Dallas) were in decline, and it would have been an all Canadian final since it had been 9 years since a team had qualified.
While not a SCF matchup, if Calgary would have won Game 7 against Anaheim in last years playoffs, there would have been a Battle of Alberta for the first time since 1991.