Best No. 1 Draft Picks Who Haven’t Won a Stanley Cup

The best No. 1 draft picks are so good they influence a team’s Stanley Cup odds at the BetMGM online sportsbook. 

Some propel their team to glory while others huff and puff but never accomplish the goal every player prioritizes.

Getting the opportunity to sip from the Holy Grail has eluded many top-tier players, and these are the best No. 1 draft picks who never won a Stanley Cup, along with those still searching.

Best First Overall Draft Picks Without a Stanley Cup

8. Pierre Turgeon (1987 – Buffalo Sabres)

Pierre Turgeon gave it his best crack, playing for six teams during his 20-year career. He arrived in Montreal one season too late, missing the Montreal Canadiens 1993 Stanley Cup run. 

While he averaged more than a point per game, Turgeon never played in the Stanley Cup Final. 

7. Taylor Hall (2010 – Edmonton Oilers)

Like Turgeon, Taylor Hall has never played in a Stanley Cup Final. However, he has a chance to break that streak with the Carolina Hurricanes, who are in the 2026 Eastern Conference final. 

The 2017-18 Hart Trophy winner has made it to two Eastern Conference finals, both with the Hurricanes in consecutive playoffs (2025, 2026). 

6. Eric Lindros (1991 – Québec Nordiques)

Eric Lindros was one of three successive Quebec Nordiques first overall picks who never won the Stanley Cup, including Owen Nolan and Mats Sundin. 

Lindros infamously refused to play for the Nordiques and instead signed with the Philadelphia Flyers. Maybe the Nordiques placed a curse on him, as the 1994-95 Hart Trophy winner only made it to one Stanley Cup Final, losing in four straight to the Philadelphia Flyers in 1997. 

5. John Tavares (2009 – New York Islanders)

The 35-year-old John Tavares doesn’t have many seasons left to win an elusive Stanley Cup. 

The former New York Islanders and Toronto Maple Leafs captain still hasn’t made it past the second round of the Stanley Cup playoffs, and the prospect of doing so with the Maple Leafs appears unlikely after the 2025-26 debacle. 

His chances will depend on Auston Matthews’ future and how quickly presumed first overall pick Gavin McKenna can get up to speed.

4. Auston Matthews (2016 – Toronto Maple Leafs)

The former Calder Trophy, Hart Trophy, and three-time Rocket Richard Trophy winner has played 10 NHL seasons and has yet to compete in a conference final. 

If he doesn’t want to become the greatest player never to win a Stanley Cup in an otherwise illustrious career, at least individually speaking, he might need to depart Toronto. 

The alternative is to find a way to form a formidable partnership with McKenna, but how will the Leafs’ draft lottery win impact Matthews’ future?

3. Mats Sundin (1989 – Québec Nordiques)

Another first overall draft pick and long-time Maple Leafs captain. Does anyone else detect a couple of trends? 

But at least Sundin played in two conference finals, losing to the Buffalo Sabres in 1999 and the Hurricanes in 2002. 

2. Joe Thornton (1997 – Boston Bruins)

Joe Thornton played the second-most games without winning a Stanley Cup (1,714). 

Only longtime teammate Patrick Marleau played more games (1,779) without sipping from the Holy Grail. 

The 2005-06 Hart Trophy and Art Ross winner participated in one Stanley Cup Final during his 25-year career. As a member of the San Jose Sharks, he lost the 2016 final to the Pittsburgh Penguins. 

Thornton played for four teams, but he spent all but 78 games with the Boston Bruins and Sharks. 

1. Connor McDavid (2015 – Edmonton Oilers)

Connor McDavid has completed 11 seasons and played in the Stanley Cup Final in consecutive years against the Florida Panthers (2024 and 2025).

His failure to jump the final hurdle isn’t due to any individual deficiency, with McDavid boasting the third-most points per game in the playoffs (1.53), trailing Mario Lemieux (1.61) and Wayne Gretzky (1.84), who won four Cups with the Edmonton Oilers.  

At least time is still on his side, as No. 97 is 29 years old. I’m convinced he’ll win a Stanley Cup, but the more uncertain question is with what team and when. 

Who’s Played the Most Games Without Winning a Stanley Cup? 

Patrick Marleau played the most games without winning a Stanley Cup (1.779). 

Who Is the Best First Overall Draft Pick in NHL History?

Sidney Crosby is the best first overall draft pick in NHL history. 

Who Is the Worst First Overall Draft Pick in NHL History?

Nail Yakupov is the worst first overall draft pick in NHL history.