The Toronto Maple Leafs have not won the Stanley Cup since 1967. Not only has no player on the roster seen the Leafs lift the Cup in their lifetime, but general manager Brad Treliving was not alive, and their head coach, Craig Berube, was under two years old. This does not mean they have not been competitive, making the playoffs in nine straight seasons. This year, they fell in the second round to the Florida Panthers. If the club is going to get over the hump, they will need breakout seasons from a few players.

The Leafs were a solid team in 2024-25. They won the Atlantic Division and finished second in the Eastern Conference. Further, they were ninth in the NHL in scoring while also sitting ninth on the power play. The defense was solid as well, as they finished tied for eighth in the NHL in goals against per game, but were also 17th on the penalty kill.

Repeating this may be a tall order. While the team was able to retain John Tavares and Matthew Knies, they lost a major part of their franchise. The Maple Leafs completed a sign-and-trade, sending Mitch Marner to the Vegas Golden Knights. This means the team now needs to replace their top point producer and the man who led the team in assists.

This will be a team effort to repeat the overall success from last year while also attempting to get over the hump and return to the Stanley Cup Final. To do that, multiple players need to break out.

Can Joseph Woll take the next step in his career?

The Florida Panthers have been to the Stanley Cup Final three straight years, lifting the Cup twice in a row. They also eliminated the Maple Leafs in two of the prior three playoff campaigns. A major reason for their success has been Sergei Bobrovsky. In the two Stanley Cup-winning campaigns, he has had a goals against average under 2.35 with save percentages over .905 in both playoff runs.

If the Leafs want to get to that level, Joseph Woll needs to breakout in the playoffs. Woll started 41 games in 2024-25, making him the primary goaltender for the first time in his NHL career. He showed he was up to the challenge, going 27-14-1 with a 2.73 goals-against average and a .909 save percentage.

Anthony Stolarz would take the top spot from Woll for the first round of the playoffs, but he was injured in the first game against the Florida Panthers.  This led to Woll getting a chance in the playoffs. He played in seven games, starting six, and struggled. He had a 3.56 goals against average and a .886 save percentage, but did have a shutout. If the Leafs want to hoist the Cup, Woll needs to contribute when it matters most.

From juniors star to NHL breakout season

Toronto Maple Leafs right wing Easton Cowan (53) plays the puck against Montreal Canadiens left wing Juraj Slafkovsky (20) during the first period at Bell Centre.
David Kirouac-Imagn Images

Making the jump from the OHL level, a junior level, to the NHL would be a massive jump. If there is a player who can do it on the Leafs, it is Easton Cowan. The former first-round pick of the team in 2023 has spent three full seasons with the London Knights in the OHL, showcasing his skills.

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Over 175 games with the Knights, he lit the lamp 84 times with 136 helpers, good for 220 points. Further, he was dominant in the playoffs, amassing 96 points in 60 playoff games in his career.

The lifelong Maple Leafs fan has played in the preseason with the NHL club in the past. He has been seen as someone who can jump to the NHL level right away. Considering his speed, playmaking ability, and shooting, he has all the talent and skill to make an impact right away in the big leagues.

Maple Leafs look for a disruptive force to breakout again

Making the jump from the OHL to the NHL can be a big challenge, but Max Domi did that successfully. He played 81 games with the Arizona Coyotes as a rookie, racking up 51 points. After a step back in the next two seasons, he broke out with the Montreal Canadiens in 2018-19, scoring 72 points with a career high 28 goals.

He has not been the same level of player since. In his two years with the Leafs, he has played in 154 games, but lit the lamp just 17  times. He has added 63 assists. Domi needs to rebound to his early career and breakthrough for the franchise. He has all the tools to be a Brad Marchand-type player. The Canadian is moving in the right direction, seeing his hit numbers improve, as well as his shots blocked. He has also been willing to engage in a scuffle when needed.

It is time for him to continue that work, while making an impact in big situations. Domi has 15 career game-winning goals, but just two in the last 154 games. He has not been the big game player in his career that the Leafs need, but with his skill set and the fact that he will be put into positions to be this player, Domi is primed to move in the right direction once again.

Toronto holds the record for the longest Stanley Cup drought, sitting at 57 seasons. Only the Buffalo Sabres and Vancouver Canucks have streaks over 50 seasons, not winning a Cup in their franchise histories. Still, they have appeared in the Stanley Cup Final during that time, something the Leafs have not done. The team has the parts to make it over the hump, but it will take a major effort.

New stars such as Cowan need to make an immediate impact. Meanwhile, players like Woll and Domi need to play at their best when the lights are the brightest.