The 13 Unlucky NHL Players With The Most Stanley Cup Finals Losses Of All Time

On Tuesday night, the Panthers successfully defended their title by beating the Oilers in the Stanley Cup Final. Edmonton’s loss meant Corey Perry ended up joining a fairly enviable club comprised of the NHL players who’ve come painfully close to winning the trophy but fell short on more than a few occasions.

Simply making it to the Stanley Cup Final is an impressive achievement, but earning the right to call yourself one of the best teams in the NHL doesn’t mean much if you end up on the losing side when everything said and done.

There are a number of players who’ve made it to the last round of the postseason on multiple occasions with a team that ultimately fell short, and these guys have the fairly dubious distinction of losing in the Stanley Cup Final more times than anyone else in history.

Gordie Howe: 7 Losses

It’s hard to make this list without racking up an impressive number of trips to the Stanley Cup Final, and Gordie Howe definitely checked that box.

The man known as “Mr. Hockey” is one of the greatest NHL players of all time, and he was a major reason the Red Wings won four Stanley Cups during his 25 seasons with the franchise.

However, he appeared in the Finals on 11 occasions and subsequently holds the record for the most losses. Four came at the hands of the Maple Leafs (1948, 1949, 1963, and 1964), another two were against the Canadiens (1956 and 1966), and the final one was courtesy of the Black Hawks in 1961.

Red Horner: 6 Losses

This one is a throwback to the point where I can’t find a picture I can use, but Red Horner was a defenseman for the Maple Leafs who made the Stanley Cup Final seven times during his 12 seasons with the team between 1928 and 1940.

Horner won The Cup in 1932, but he closed out his career with a skid of six losses in the Finals in the span of eight years starting in 1933.

Busher Jackson: 6 Losses

Busher Jackson was teammates with Horner on the Maple Leafs for ten seasons and also in Toronto for the entirety of the aforementioned run that earned his spot here.

Bert Olmstead: 6 Losses

Bert Olmstead spent 14 years in the NHL while splitting his time between the Canadiens, Maple Leafs, and Black Hawks.

He won the Stanley Cup four times with Montreal and got another in Toronto, but he also lost in the Finals as a member of the Canadiens on four occasions (a stretch where they lost four times in five years between 1951 and 1955 with a championship sandwich in between).

He also suffered two losses courtesy of his former team when he was with the Maple Leafs due to back-to-back defeats to the Habs in 1959 and 1960.

Corey Perry: 5 Losses

Everyone else represented here has lost in the Stanley Cup Final five times, and we’re going to kick things off with the most recent addition.

Corey Perry has the distinction of being the only player in NHL history to lose in the Stanley Cup Final with four different teams—a feat he only needed four seasons to achieve.

He was on the Stars when they lost to the Lightning in The Bubble in 2020, joined the Canadiens before they fell to the same opponent the following year, decided to chase a ring with Tampa Bay before they lost to the Avalanche in 2023, and then got handed back-to-back defeats thanks to the Panthers after heading to Edmonton.

Perry can take some solace in winning a Stanley Cup with the Ducks in 2007, but that’s still gotta sting.

Alex Delvecchio: 5 Losses

Alex Delvecchio spent the entirety of his 24-season career with the Red Wings and played alongside Howe for the bulk of that stretch.

He got his name etched on the Stanley Cup for the first of three times in 1952 to cap off what was effectively his rookie season (he’d made his NHL debut in the single game he played during the 1950-51 campaign) but was also with Detroit for those five losses between 1956 and 1964.

Doug Harvey: 5 Losses

Doug Harvey joined the Canadiens shortly before they kicked off the stretch of Stanley Cup Final losses I discussed while talking about Olmstead, and he and the Blues were swept by Montreal in 1968.

However, he did get six Stanley Cups with the Habs before the team’s GM shipped him off to the Rangers out of spite; he cited his lackluster play in the postseason in 1961 but was also not happy he had started to lobby for higher salaries for players.

Murph Chamberlain: 5 Losses

Murph Chamberlain played for the Maple Leafs, Bruins, and Canadiens (he also had a brief stint with the Brooklyn Americans) and got two Stanley Cups while capping off his 12-year career with Montreal.

However, Toronto lost three years in a row when he was on the team (a streak that began in 1938), and he also came up short with Boston in 1943 and Montreal in 1947.

Regis "Pep" Kelly: 5 Losses

All of the guys we’ve mentioned so far got a consolation prize by winning at least one Stanley Cup, but that’s sadly not the case for the rest of the players on this list.

That includes Regis “Pep” Kelly (another guy who is elusive on the photo front), who made it to the Stanley Cup Final with the Maple Leafs five times between 1935 and 1940 only to be dispatched by five different teams during that run.

Bruce MacGregor: 5 Losses

Bruce MacGregor kicked off his NHL career with the Red Wings at the start of the 1960s and spent 11 years in Detroit before heading to the Rangers for four more seasons.

He got his first taste of the Stanley Cup Final (and his first loss there) as a rookie and ended up befalling the same fate four times during his first six years in Detroit.

He had another shot to get a Stanley Cup in New York in 1972, but the Rangers fell to the Bruins in the Final.

Gerry Melnyk

Gerry Melnyk is one of the more fascinating entries on this list, as his NHL career technically only lasted for four years if you only take regular season games into consideration.

However, he appeared in the postseason six times, which included an NHL debut that came after the Red Wings made the playoffs in 1956 before Montreal beat them to win the Stanley Cup

They lost again during his last season in Detroit in 1961, he lost again when the Black Hawks fell to the Maple Leafs the following year, and he capped off his career with the Blues before they were defeated by the Canadians in 1968.

Brian Propp

Brian Propp was basically the original version of Corey Perry, as he spent 15 years in the NHL and made it to the Stanley Cup finals five times with three different teams.

He came up short three times with the Flyers between 1980 and 1987, lost again when the Oilers beat the Bruins in 1990, and got the same treatment when the Penguins beat the North Stars during his penultimate season in 1991.

Norm Ullman

We’re wrapping things up with Norm Ullman, the Hall of Famer who spent 20 years in the NHL while splitting his time between the Red Wings, Maple Leafs, and Oilers.

Detroit was the culprit for all five of his losses, as they fell short in 1956 prior to the aforementioned quartet of defeats in the 1960s.