The 11 NHL Players Who Had To Wait The Longest Before Winning Their First Stanley Cup

Every NHL player grows up dreaming about the day they earn the right to raise the Stanley Cup. Most of them will never get the chance to realize it, and there are some others who had to wait a very long time before it finally came true.

These are the NHL players who played the most games before winning a Stanley Cup

The Stanley Cup has a history that stretches back before the NHL’s inaugural season in 1917.

It was initially commissioned in 1892 so it could be handed out to the best amateur hockey team in Canada on an annual basis, and it was eventually used to crown the best pro teams in North America before the NHL essentially claimed the rights to it ahead of the 1926-72 season (it became its official championship trophy a couple of decades later).

Close to 3,500 names had been engraved on the Stanley Cup prior to the start of the postseason in 2026. Some players are lucky enough to check that box as a rookie, but others have had to wait the majority of their career (including a few who finally got a title in their final NHL game) before winning it.

11. Kimmo Timonen: 1,108 Games

There are currently 19 players who played at least 1,000 games in the regular season before winning their first Stanley Cup, and 11 of them needed to wait a minimum of 1,100 games before getting over the hump.

That includes Kimmo Timonen, the five-time All-Star who kicked off his career with the Predators in 1998.

Nashville made it to the playoffs three times during the eight seasons the Finnish defenseman played with the franchise but was unable to get it done. He also fell short on six occasions during the seven seasons he spent with the Flyers (which included a loss to the Blackhawks in the Stanley Cup Final in 2010).

Timonen missed the majority of the 2014-15 season with blood clots that kept him out of action until the start of March, but he got a chance to chase a title with the team that had previously denied him of one after Philly traded him to Chicago.

He’d announced his plans to retire upon the conclusion of the season, and he ended his career on a high note after the Blackhawks dispatched the Lightning in six games.

10. Lanny McDonald: 1,111 Games

Lanny McDonald got a taste of the postseason during five of the seven years he spent with the Maple Leafs after joining the club as a rookie in 1975. However, as Toronto fans are painfully aware of, none of those runs ended with a Stanley Cup (or, for that matter, an appearance in the final).

He failed to return to the playoffs during a stint with the Colorado Rockies, but he had a bit more success on that front after he was traded to the Flames in 1981. Calgary only missed the playoffs a single time during the nine seasons he was there, which included an appearance in 1989 during what McDonald had privately decided would be his final NHL season.

The Flames ended up meeting the Canadiens in the Stanley Cup Final, and while the winger was kept out of the lineup in the three games leading up to Game 6, head coach Terry Crisp not only penciled him in but named him the captain with the chance to clinch the series with a 3-2 lead.

McDonald scored his only goal of the postseason to help his team get the 4-2 win and retired as a Stanley Cup champion.

9. Steve Duchesne:1,113 Games

There are two guys on this list that saw their long-awaited wait come to an end with the Red Wings in 2002, and the first one is Steve Duchesne.

The d-man bounced around the league a fair amount during a 16-year NHL career he ushered in with the Kings in 1986. The three-time All-Star also had stints with the Flyers, Nordiques, Blues, and Senators before landing in Detroit in 1999 to kick off a three-year run that would end up being his swan song.

The Red Wings were treated to a couple of fairly quick exits in the playoffs in 2000 and 2001, but they returned with a vengeance in 2002 as a top-seed that met the Hurricanes for all the marbles.

Duchesne didn’t have a huge impact in a series where he only recorded a single assist while logging ten penalty minutes, but he still got his name etched on the Stanley Cup after his squad pulled off the gentleman’s sweep by winning in five games.

As was the case with everyone we’ve mentioned so far, he also hung up his skates after the season.

8. Andrew Cogliano: 1,140 Games

Andrew Cogliano is the most recent addition to this list. The veteran forward did not have any luck during the 14 seasons he split between the Oilers, Ducks, Stars, and Sharks before he was shipped off to the Avalanche ahead of the trade deadline in 2022.

San Jose was gracious enough to give him a chance to chase a championship with a contender, and he was able to take full advantage. He overcame a broken finger he suffered while blocking a shot in the conference finals to suit up against the Lightning, and he had a goal and two assists in the series Colorado ended in six games.

We’re breaking with the pattern here, as Cogliano spent two more seasons with the Avs before calling it quits.

7. Jay Bouwmeester: 1,184 Games

Jay Bouwmeester won back-to-back gold medals while skating for Canada at the World Championships in 2003 and 2004 and added another to his collection at the Winter Olympics in 2014, but it seemed like he may never join the fairly exclusive club currently comprised of the 30 players who’ve checked both of those boxes and won a Stanley Cup.

The defenseman entered the league with the Panthers in 2002 and spent six seasons there ahead of a four-year run with the Flames. However, he had not gotten the chance to play in a single Stanley Cup Playoff game by the time he was traded to the Blues in the second half of the season in 2013.

He got to experience playoff hockey for the first time that year, which marked the first of six times St. Louis punched its ticket to the postseason during his tenure. 2019 was the first time they made it to the Stanley Cup Final, and they dispatched the Bruins in seven games.

Bouwmeester returned the following season, but he suffered a heart attack on the bench during a game on February 11, 2020 and decided to retire as a result.

6. Rod Brind’Amour: 1,187 Games

Rod Brind’Amour is still in search of his first Stanley Cup win as a coach, and he can only hope it won’t take him as long to get one as it did when he was playing.

The center debuted with the Blues in 1989 but only spent a couple of seasons in St. Louis before he was traded to the Flyers. He spent a decade in Philadelphia during a span that spawned five fruitless trips to the playoffs, and he headed down to Carolina after they traded him to the Hurricanes in 2000.

As I mentioned above, they made it to the Stanley Cup Final in 2002 before losing to the Red Wings, but Brind’Amour got another shot against the Oilers in 2006. It took them seven games, but they won in a series where Brind’Amour scored three goals (including two in a 5-4 victory in Game 1).

He hung around for four more seasons, but that ended up being the only time his name was etched on the Stanley Cup (at least for now).

5. Luc Robitaille: 1,205 Games

Remember when I said two guys brought their lengthy wait to an end with the Red Wings in 2002? Luc Robitaille was the other one.

The winger spent the bulk of his 19-year career with the Kings (starting it in Los Angeles in 1986 and ending it there in 2006), but he also had some shorter stints with the Flyers, Penguins, and Red Wings.

Robitaille actually made the playoffs 15 times, but the run with Detroit in 2002 was the only time one of those appearances ended with a championship. However, the man who currently serves as the president of the Kings also had his name engraved on the Stanley Cup for his work in the front office during their title runs in 2012 and 2014.

4. Pat Verbeek: 1,225 Games

Pat Verbeek was a bit of a journeyman who kicked off his NHL career with the Devils in 1983, and he also played for the Whalers, Rangers, Stars, and Red Wings during his 20 years in the league.

He had two separate runs with Dallas and was still in search of a Stanley Cup when he arrived as a free agent ahead of the 1996-97 campaign. They made the playoffs during his first two seasons, and while they extended that streak to three years in a row in 1999, he was forced to miss the first round with a knee injury.

The Stars managed to get to the second one without him, but he quickly found himself sidelined again due to the one-game suspension he was hit with over a slashing penalty. He managed to avoid any further issues for the remainder of the playoffs, and he contributed three goals and four assists during a run that ended with Dallas defeating the Sabres in six games after Brett Hull sealed the deal with a controversial goal in triple overtime.

3. Glen Wesley: 1,311 Games

Glen Wesley played in the Stanley Cup Final four times during his 20-year career, and the fourth time ended up being the charm for the man who had previously come up short with the Bruins during his rookie season in 1988 and once again a couple of years later (with both defeats coming at the hands of the Oilers).

He was traded to the Whalers in 1995 and was still on the team when they became the Hurricanes. He was a member of the squad that lost to the Red Wings in 2002, but the defenseman got his long-awaited title in 2006 and spent two more seasons in Carolina before retiring.

2. Dave Andreychuk: 1,597 Games

Dave Andreychuk spent the bulk of his 23-year career as a member of the Sabres, but he played for six different franchises while capping things off with the Lightning after making the fairly surprising decision to sign with Tampa Bay in 2001.

Most people assumed the 38-year-old would join forces with a team that clearly had the talent to contend for a Stanley Cup, which was not the case with the Lightning when he arrived. The team was in the midst of a five-year playoff drought that stretched to six upon his arrival, but he was named their captain ahead of the 2002-2003 season before leading them to the conference finals.

The Bolts picked up where they left off the following year and punched their ticket to the Stanley Cup Final for the first time in franchise history before defeating the Flames in seven games. Andreychuk was eventually immortalized with a statue outside their arena, and he returned for one last ride in the wake of the lockout before retiring after being waived in 2006.

1. Ray Bourque: 1,612 Games

Ray Bourque cemented himself as one of the best defensemen in NHL history during the 21 seasons he played with the Bruins, and it seemed like he was both destined to spend his entire career in Boston and bring it to an end without winning a Stanley Cup.

However, the team traded him to the Avalanche in March of 2000 after it became clear he probably wasn’t going to get it done with them, and the move to Colorado was a purposeful one that provided him with a golden opportunity to finally get the title he’d spent more than two decades chasing.

The Avalanche fell short that season, but they were able to make it to the Stanley Cup Final in 2001 and beat the Devils in seven games. The captain of the winning team is traditionally the first player to take a lap with the trophy, but Joe Sakic immediately handed it to Bourque when he received it.

Bourque retired in the wake of the win, and he had his number retired by both the Bruins and the Avalanche despite playing less than two seasons for the latter.