Actually, the Montreal Canadiens championship streak was to go no longer than 6 years without a Stanley Cup. Somehow, someway, they always won a cup within 7 years of the last one. This amazing streak had been in effect since the 1943-44 season. However, that streak is now dead. The 1999-2000 season was 7 years after the last Stanley Cup win (as mentioned above, 1992-93 season) and the Canadiens failed to win the championship that year.
In fact, by failing to even make the playoffs that year, it meant that the Canadiens missed the playoffs in consecutive seasons. Amazingly, the last time the Montreal Canadiens failed to make the playoffs in consecutive season was the 1920-21 season and the 1921-22 season (back when there were only 4 teams (Montreal Canadiens, Ottawa Senators(the original incarnation), Toronto St. Pats (became the Maple Leafs), and Hamilton Tigers (defunct))).