The Stanley Cup is the most elusive prize in professional sports, and even some of the NHL’s greatest talents are still chasing it. Whether it’s due to bad luck, tough playoff exits, or just being part of a rebuilding franchise, some of today’s most elite players are still missing that one critical line on their résumé. Here’s a look at the best active NHL players who’ve never hoisted the Cup — yet.
1. Connor McDavid – Edmonton Oilers
It almost feels criminal to put McDavid on this list. Widely regarded as the best player on the planet, McDavid has collected multiple Hart Trophies, Art Ross titles, and highlight-reel plays that defy physics. Yet, despite his brilliance, the Oilers haven’t made it past the Western Conference Final during his tenure, and questions about the supporting cast and goaltending linger. If he doesn’t win a Cup, it would be one of the greatest “what-ifs” in NHL history.
2. Leon Draisaitl – Edmonton Oilers
The perfect 1B to McDavid’s 1A. Draisaitl is a former Hart winner in his own right and is arguably the best goal-scoring power forward in the game. His playoff performances have been electric — at times even outshining McDavid — but like his teammate, he’s still chasing the ultimate team prize.
3. Auston Matthews – Toronto Maple Leafs
A generational goal scorer and the 2022 Hart Trophy winner, Matthews is the cornerstone of Toronto’s long-suffering quest to bring the Cup back north of the border. The Leafs finally won a playoff round in 2023, but early exits continue to define the core’s tenure. Matthews is a game-breaker, but time is ticking for this group to prove they can win when it counts.
4. Igor Shesterkin – New York Rangers
Since taking over the crease in New York, Shesterkin has emerged as one of the league’s most dominant goaltenders, winning the Vezina Trophy in 2022. He’s had deep playoff runs but hasn’t gotten over the hump. Given his talent and the strength of the Rangers’ roster, his window is still wide open.
5. David Pastrnak – Boston Bruins
Pastrnak has had individual success — including a 60-goal season and multiple All-Star appearances — but came up just short in the 2019 Final and suffered an epic first-round collapse after a historic 2022–23 regular season. He’s the face of the Bruins’ next era and one of the NHL’s most dangerous snipers.
6. Roman Josi – Nashville Predators
Josi is one of the league’s most complete defensemen — a Norris Trophy winner and the heart of the Predators’ franchise. He helped lead Nashville to the 2017 Final but came up short. Now 34, his window may be closing, but his talent hasn’t faded.
7. Artemi Panarin – New York Rangers
One of the most creative and consistent offensive forces in the NHL, Panarin has had stellar regular seasons, but playoff success has been elusive. He’s been a core piece for a Rangers team that feels on the verge — but “almost” won’t be enough for a player of his caliber.
8. Elias Pettersson – Vancouver Canucks
Still early in his prime, Pettersson has quietly evolved into one of the league’s top two-way centers. The Canucks are trending up, but they’ve yet to break through in the postseason. With Pettersson, Hughes, and Demko, the core is promising — but the Cup remains out of reach.
9. Thatcher Demko
Can steal a series, but health and team depth remain question marks.
10. John Tavares
Still searching after more than a decade in the league.
Final Thoughts
Some of these players still have time on their side; others are running out of chances. What unites them is undeniable talent and the shared hunger to etch their names into hockey immortality.
Who do you think will be the next to break through and win their first Cup?
