How Many Stanley Cups Did Sidney Crosby Win?

Posted on May 20, 2024 by Dan Kent
How Many Stanley Cups did Crosby Win

Sidney Crosby, a renowned ice hockey player from Canada, made his NHL debut in the 2005-06 season with high expectations and the nickname "Sid the Kid." 

Over the years, Crosby has lived up to the hype, achieving numerous accolades and titles. He will undoubtedly become one of the greatest players ever to touch the ice. 

I remember I was 14 years old when he was drafted, jealous that my own Edmonton Oilers didn't end up winning the NHL Draft lottery to take him.

Crosby would go on to become the youngest player ever to record 100+ points in the NHL and would also become the youngest captain in NHL history.

It is likely Sidney Crosby's first team, and his only team, will be the Pittsburgh Penguins, as he is getting to the latter portion of his NHL career.

How many Stanley Cups has Crosby won?

Among his many accomplishments, Crosby has secured three Stanley Cups with the Pittsburgh Penguins. He's played a pivotal role in every single one of them, which is why he'll go down as one of hockey's greats.

Throughout his career, Crosby's extraordinary skills have earned him a reputation as one of the most valuable players in the sport. As captain of the Pittsburgh Penguins, he has led his team to victory in various prestigious cup finals.

Whether they've been the favourite or the underdog, there is one thing for certain. Crosby will show up game in and game out. 

Excelling in various aspects of the game, Crosby has shattered records and received various awards, including the Art Ross Trophy, Rocket Richard Trophy, and multiple Hart Memorial Trophies. 

Despite facing challenges, such as injuries and concussions, Crosby's greatness on the ice continues to shine, further solidifying his legacy as one of the greatest ice hockey players in recent history.

Lets go over his Stanley Cups.

Stanley Cup #1 2008-09 Pittsburgh Penguins vs Detroit Red Wings – Penguins in 7 games

This iconic Stanley Cup series was a rematch of the previous year's finals, where the Detroit Red Wings had won in six games. As times changed, the Red Wings' dominance began to fade, leading to the emergence of the Pittsburgh Penguins and their star player, Sidney Crosby.

This is an interesting note about this series and one I find a bit funny. Marian Hossa, a likely Hall of Fame NHL player, would be traded to the Penguins during the 2007-2008 season and lose in the finals to the Red Wings. 

He would then jump ship, signing with the Detroit Red Wings for the 2008-2009 season, only to lose that series in seven games to the Pittsburgh Penguins: two straight cup finals, both on the wrong side of the coin.

But I wouldn't feel too bad for him. He would go on to win three Stanley Cups with the Chicago Blackhawks. However, let's get back to the series.

The series seemed to favor the Red Wings once again, as it was tied 2-2 and Detroit delivered a crushing 5-0 victory in Game 5. But the Penguins were not done yet. They managed to win Game 6 with a 2-1 defensive battle, leading to a decisive Game 7 in Detroit.

In Game 7, the Penguins once again engaged in a tight defensive match, led by the outstanding performance of their goalie, Marc-André Fleury, who made crucial saves in the final minutes. Pittsburgh secured their Stanley Cup victory with a final score of 2-1.

Throughout the playoffs, Sidney Crosby displayed rock-solid leadership and the desire to win. However, it was his teammate Evgeni Malkin who won the Conn Smythe trophy as the most valuable player. 

Crosby's presence allowed Malkin more opportunities to excel against weaker competition. Having two superstars on the same team truly bolstered the Penguins' performance. It showed why it's so important to have multiple strong centermen.

Crosby would accumulate only 3 points in the seven-game series.

This memorable 2008-09 Stanley Cup series marked a turning point in the NHL, as the Pittsburgh Penguins dethroned the Detroit Red Wings and established themselves as a new force to be reckoned with.

Stanley Cup #2 2015-16 Pittsburgh Penguins vs. San Jose Sharks – Penguins in 6 games

The 2015-16 season saw a much-anticipated return to the Stanley Cup stage for the Pittsburgh Penguins, six years after they secured their first win under Sidney Crosby's leadership and Evgeni Malkin's dominance. 

This time, they faced the San Jose Sharks, a team that experienced its fair share of playoff letdowns. Despite a competitive Sharks lineup, the Penguins exhibited control throughout the series, ultimately emerging victorious in 6 games. This would be the San Jose Sharks, who have never won a Stanley Cup, only appearance in history.

Throughout the 2015-16 playoffs, Sidney Crosby demonstrated exceptional prowess on the ice, and the finals were no exception. Crosby showcased his unparalleled all-around skills that contributed to the team's success.

For his outstanding performance, Crosby received his first-ever Conn Smythe trophy as the playoff MVP.

He would only accumulate four points in the finals. Still, I remember watching the Penguins cup run during this time. There was absolutely no doubt his combination of offence, defence, and leadership was worthy of an MVP title.

This successful playoff run solidified Crosby's reputation as a dominant force in the league. It marked an important chapter in the Penguins' storied history. 

By capturing their second Stanley Cup win in the Sidney Crosby era, the Penguins once again proved their status as a premier hockey team and set the stage for continued greatness in the years to come.

Stanley Cup #3 2016-17 Pittsburgh Penguins vs Nashville Predators – Penguins in 6

In a rare feat, the Pittsburgh Penguins secured back-to-back Stanley Cup victories.

Despite the Washington Capitals being the initial favorites, the Penguins eliminated them in a thrilling seven-game series during the second round. The whole Crosby/Ovechkin rivalry was a thing to watch as both of these players dominated the league in their prime.

They went on to face the Senators in the Eastern Conference Finals, culminating in a showdown against the Nashville Predators, who were making their Stanley Cup Finals debut.

Throughout the series, the Penguins' victory seemed almost inevitable. Though the Predators kept the competition close, the Penguins' extensive experience shone through, allowing them to secure crucial wins. True to form, the Penguins won the Cup, once again on their opponent's ice, in Game 6.

As for Sidney Crosby, the Penguins' heart and soul, he achieved a rare accomplishment. Joining the ranks of Bernie Parent and Mario Lemieux, Crosby was awarded the Conn Smythe Trophy for the most valuable player in the playoffs for the second consecutive year. 

This would also be his highest scoring Cup winning series. He'd record seven total points in the six games played.

This impressive display highlighted Crosby's vital contributions to the team as the Pittsburgh Penguins secured their third Stanley Cup against the Nashville Predators.

Is three Stanley Cups even that good?

Winning three Stanley Cups in one's career is an incredible achievement, especially in today's competitive NHL landscape. 

With the business side of hockey making it more challenging to build and maintain winning teams, securing multiple championships is certainly praiseworthy.

Considering other all-time hockey greats, like Wayne Gretzky, who won four Stanley Cups, and Mario Lemieux, who won two, achieving three championships puts a player in an elite group in NHL history. 

Sidney Crosby, for instance, was able to capture his first Cup in just his fourth year in the league—a remarkable accomplishment.

In my opinion, the players with many more cups than Crosby often did it when the league was much smaller. For the players who accomplished 3 or more wins in a modern-sized NHL league, it is a remarkable accomplishment.

As time passed, many wondered if Crosby will secure another championship. It looks unlikely now as the Penguin's best days are likely behind them, with aging veterans like Kris Letang and Evgeni Malkin not getting any younger.

But his back-to-back Stanley Cup victories solidified his place among the game's greats, such as Gordie Howe and Bobby Orr. Throughout their careers, these legends have won numerous accolades and awards. Still, it is the Stanley Cup triumphs that they treasure most.

Let’s not forget the gold medal

Not only would Crosby go on to win three Stanley Cups throughout his NHL career, he would score the game-winning goal in overtime to take home the gold medal at the 2010 Winter Olympics in Vancouver, Canada.

The goal is still referred to today as the "Golden Goal." Although Crosby was never known as a premiere goal-scorer like Alex Ovechkin, he still knew how to put the puck in the net routinely.

Olympic gold medals are an accomplishment that many never achieve. But to score in overtime in your home country, I'd say Crosby will likely remember this moment more than any of his goals in the Stanley Cup Playoffs.

Dan Kent

About the author

Growing up in a hockey hotbed (Calgary, Alberta. And yes, I'm an Oiler fan), I decided to put my love and knowledge of the game to work. I started at five and am still playing today into my early 30s. By acquiring Brave Stick Hockey and rebranding it to Big Shot Hockey in 2023, I plan to teach people about this great game and educate them on the best equipment and history of the game. On a career level, I am in finance, running one of the largest financial websites in Canada,

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