Why the Toronto Maple Leafs Will Win the Stanley Cup
The Toronto Maple Leafs have the longest Stanley Cup title drought in the NHL, but Auston Matthews & Co. are capable of ending that this postseason if the Leafs get reasonably good goaltending. Here’s why the Leafs may hoist Lord Stanley’s Cup in June.
Sheldon Keefe’s Job On Line?
Easily the longest Stanley Cup drought in the NHL belongs to Toronto, which last won it in 1966-67 to cap a run of four titles in six seasons. The Maple Leafs haven’t even been back since then. The second-longest droughts belong to the Vancouver Canucks and Buffalo Sabres, who both joined the NHL for the 1970-71 campaign. Buffalo currently has the league’s longest playoff drought. Vancouver is the Pacific Division champion and has a very realistic shot at the 2024 Cup. A Canucks-Maple Leafs Final matchup is priced +5000.
There is a lot of speculation that Leafs coach Sheldon Keefe will be a goner if the team doesn’t get to at least the conference finals. Yes, Toronto finally got past the first round for the first time since 2004 last April with a six-game win over Tampa Bay but then was dominated in a five-game loss to wild-card Florida. Keefe has a terrific 212-97-40 regular-season record in Toronto but 13-17 in the playoffs. The Leafs’ 102 points this season were their fewest in a full season under Keefe.
Leafs’ Opponent Changed Late
For weeks, it looked as if Toronto would be opening the first round of the Stanley Cup playoffs at Florida as the Panthers had been in second in the Atlantic Division and Boston in first. However, the Bruins were upset twice this week at Washington on Monday and in a truly unforgivable stunner, 3-1 at home against Ottawa on Tuesday. Win either and the B’s take the Atlantic. Florida’s 5-2 home win over the Leafs on Tuesday gave the division to the Panthers and they now open vs. Tampa Bay.
Toronto goes to Boston for Game 1 on Saturday in the 17th all-time playoff meeting between the Original Six franchises and first since 2019. They have split the previous 16, but Boston has won the past six playoff series vs. Toronto. On the series line, Boston is -120 and the Maple Leafs +100. The favoured exact result is Bruins in seven at +425 followed by Leafs in six at +450. The Bruins winning Game 1 and the series is +160, and the Leafs doing it is +200.
Boston also won all four regular-season meetings against Toronto, which didn’t score more than three goals in any of them. And therein lies the issue with justifying taking the Leafs at +1400 to win the Cup: High-powered offensive teams these days without a star goaltender rarely win the Cup. Ask Edmonton.
Offensive Firepower

Toronto has the offensive firepower to beat anyone led by Auston Matthews, who crushingly came one goal shy of becoming the ninth player in league history to score 70 in a season as he failed to find the net in the team’s final two games. The Leafs finished second in the NHL in scoring at 3.63 goals per game. However, only 11 teams finished with a worse goals-against average than Toronto’s 3.18 mark.
The only one of the 11 in the playoffs is Tampa Bay, which allowed 3.26 goals per game. The Lightning also have an all-world, future Hall of Fame goalie in former Conn Smythe Trophy winner Andrei Vasilevskiy. He missed a chunk of the season injured and then took some time to shake the rust off. That’s why such a high team GAA. Toronto doesn’t have anyone in his class – presumably, Ilya Samsonov will start the postseason as the No. 1 guy. He allowed 11 goals in his final two regular-season starts.
Which East matchup would Toronto even be close in goal? Certainly not against Boston with its duo of Jeremy Swayman (utterly dominated the regular-season series) and Linus Ullmark. Florida in a potential second-round matchup has the big edge in Sergei Bobrovsky. We mentioned the Lightning. The Rangers have former Vezina winner Igor Shesterkin and the Hurricanes former Leafs No. 1 Frederik Andersen. New York and Carolina were the top two teams in the Metropolitan Division.
While Toronto likely will not have home-ice advantage for any playoff series, the Leafs were one of the NHL’s best teams on the road at 24-11-6. The shortest odds for an opponent opposite Toronto in the Stanley Cup Final is against Colorado, Dallas and Edmonton all at +2800. But the shortest exact Cup result odds with Toronto winning is +5000 over the Stars.
Long story short: Unless Samsonov (or Joseph Woll) stands on his head, Toronto’s Cup drought will continue.
