HISTORIC HEARTBREAK LOOMS: Corey Perry Faces Potential Fifth Straight Stanley Cup Final Loss with Fourth Different Team Since 2007 Triumph
When Corey Perry lifted the Stanley Cup with the Anaheim Ducks in 2007, few could have predicted the bizarre and painful postseason trajectory his career would take nearly two decades later. At just 22 years old, Perry was part of a young, talented Ducks team that surged to glory with grit, speed, and skill. That victory, at the time, seemed like it might be the first of several for the gifted winger. But now, in 2025, the veteran forward stands on the precipice of an unwelcome distinction: if the Edmonton Oilers lose their next game in the Stanley Cup Final against the Florida Panthers, Perry will have lost five straight Cup Final appearances with four different teams. It’s a staggering, almost cruel twist in the legacy of a player whose postseason résumé is equal parts remarkable and heartbreaking.
To understand the gravity of this situation, it’s important to examine Perry’s winding path through hockey’s ultimate stage. After winning it all with Anaheim, Perry would go on to establish himself as one of the league’s premier power forwards. A Hart Trophy winner in 2011, he led the NHL in goals and was widely regarded as a clutch playoff performer. For years, he was the centerpiece of Anaheim’s offense and a consistent threat come springtime. But as the Ducks began to decline and injuries mounted, Perry’s time in California came to an end. What followed was a series of short stints with contending teams, each one bringing him tantalizingly close to reclaiming the Cup—only for it to slip from his grasp in devastating fashion.
His string of Final defeats began in 2020 with the Dallas Stars. In a COVID-19-disrupted season that saw the playoffs take place inside a bubble in Edmonton, Perry and the Stars made a surprise run to the Final. The veteran winger was a key contributor throughout the postseason, scoring big goals and bringing the sort of grit and experience that Dallas needed. But despite a valiant effort, the Stars were outmatched by the Tampa Bay Lightning, falling in six games. Perry’s contributions were lauded, but the result was the first of what would become a string of painful near-misses.
He returned to the Final the very next year in 2021, this time as a member of the Montreal Canadiens. That improbable run captivated the hockey world, as the underdog Habs stormed through the North Division and shocked heavily favored opponents en route to the Final. Once again, Perry’s presence was felt—he brought leadership, timely offense, and a hard-nosed attitude that embodied playoff hockey. But once again, the Lightning stood in his way. Tampa’s relentless skill and depth proved too much for Montreal, and the Canadiens were dispatched in five games. For Perry, it was another opportunity lost, another chance at glory extinguished.
Incredibly, the pattern repeated itself in 2022 when Perry signed with the very team that had twice thwarted him—Tampa Bay. Many believed this would be the year the curse broke, that by joining forces with the juggernaut Lightning, Perry would finally get his redemption. He fit in well with Tampa’s veteran core and helped propel them back to the Final. This time, their opponent was the Colorado Avalanche, a team brimming with young talent and offensive firepower. It was a fierce, high-paced series, but ultimately, the Avalanche prevailed in six games. For Perry, it was a third consecutive Final loss, each one coming with a different team, each one compounding the agony.
After spending another season with Tampa, Perry found himself taking a different path. Eventually, he signed a short-term deal with the Chicago Blackhawks, where he played a mentorship role with Connor Bedard before being let go midseason due to internal disciplinary reasons. Many assumed his days of deep playoff runs were over. But the Edmonton Oilers, desperate to bolster their bottom-six experience and locker room leadership, brought him in. It was a gamble, but one that paid off as the Oilers surged through the Western Conference playoffs. Powered by the offensive brilliance of Connor McDavid and Leon Draisaitl, and buoyed by timely contributions from veterans like Perry, Edmonton reached the Final for the first time since 2006.
Yet, now the Oilers are on the brink of elimination once again. Down 3-1 to the Florida Panthers, Edmonton faces a do-or-die Game 5 on the road. Should they fall short, Perry will have lost a staggering five consecutive Stanley Cup Finals since 2020. It’s a stretch of futility that defies logic, especially for a player who continues to find ways to contribute in meaningful games. While much attention is rightly focused on stars like McDavid and Draisaitl, the narrative surrounding Perry is quietly becoming one of the most astonishing in modern NHL history.
What makes this string of Final losses so unique isn’t just the quantity—it’s the variety. Losing in the Final is painful no matter what, but to do it five times, with four different teams, in four very different circumstances, is virtually unheard of. For Dallas and Montreal, he was part of an underdog team fighting uphill battles. In Tampa, he joined an established power and came up just short. Now in Edmonton, he’s part of a talented squad still learning how to get over the championship hump. In each case, the common denominator is Perry—and not because he failed to perform. On the contrary, he has regularly shown up in big moments. But the hockey gods, it seems, have dealt him a cruel hand.
There’s also a certain irony to the fact that Perry’s 2007 Cup win came so early in his career. At the time, it seemed like a natural beginning to a long run of championships. He was young, gifted, and surrounded by elite talent. But that moment remains his only Stanley Cup triumph, a distant memory that now stands in stark contrast to the heartbreaking losses that have followed. Some fans have even begun to call it a “curse,” joking—sometimes with sympathy, sometimes with sarcasm—that Perry’s mere presence dooms teams in the Final. But anyone who has watched him play knows the truth: Perry’s postseason experience and gritty style of play are assets. His losses are not indictments of his performance, but reminders of how difficult it is to win it all in today’s NHL.
Should the Oilers fall to the Panthers in Game 5, Perry’s legacy will take on yet another layer of complexity. For most players, reaching one Stanley Cup Final is a dream. To reach six is a rare feat. To win one and lose five straight would be a paradox—a mix of incredible durability and heartbreaking outcomes. Perry would become the embodiment of both triumph and tragedy, a player whose career is defined as much by resilience and perseverance as it is by early glory.
Yet, there’s also something to be admired in Perry’s story. He continues to find ways to contribute. He remains in demand, even late in his career. Coaches trust him in key moments. Teammates respect his battle-tested leadership. He’s not coasting on reputation—he’s still earning his minutes. That, perhaps more than any championship ring, is the true measure of a competitor. He’s not just chasing a second Cup. He’s giving everything he has, every shift, every game, in pursuit of it.
And it’s not over yet. As the Oilers prepare for Game 5, Perry has one more chance to stave off history. One more opportunity to delay the final chapter in what could be one of the most bittersweet careers in NHL lore. Edmonton has shown resilience before—they’ve faced adversity and bounced back. And with their backs against the wall, they’ll need every ounce of experience, determination, and leadership they can muster. Perry, more than most, understands what it takes to survive in the playoffs. He’s been here before. Too many times.
Whatever happens next, Corey Perry’s journey stands as a testament to the volatility of sport. He is a reminder that greatness isn’t just measured in rings, but in the willingness to keep coming back, to keep fighting, to keep believing. Five straight Cup Final losses would be a cruel and unusual footnote on a brilliant career—but it would also highlight the remarkable consistency and drive that’s brought him to the cusp of glory, time and again. Whether he finally breaks the curse or becomes an unwilling symbol of heartbreak, one thing is certain: Corey Perry’s story is unlike any other, and the hockey world will be watching closely to see how it ends.
