The Montreal Canadiens were the last Canadian team to hoist the Stanley Cup when they did so during the 1992-93 season. It's been an agonizingly long drought for the country that has seven teams in the league to go without winning the sport's most coveted prize.

While the Maple Leafs are making their ninth consecutive appearance in the Stanley Cup Playoffs, the Senators are in the postseason for the first time since 2017 when they lost in double overtime in Game 7 of the Eastern Conference Final to the eventual Stanley Cup champion Pittsburgh Penguins.