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.

The Maple Leafs have qualified for the playoffs each of the past nine seasons but with only one series victory in that span. They lost in seven games to the Boston Bruins in the first round last season. The Senators last made the playoffs in 2017, when they lost to the Pittsburgh Penguins in seven games in the conference final.

The Maple Leafs secured the North division crown in 2021 during the COVID-19 season, but this was clearly different. With a fresh head coach who implemented new systems, Toronto f